17-Amino-10-oxo-3,6,12,15-tetraoxa-9-azaheptadecanoic Acid CAS#: 1143516-05-5; ChemWhat Code: 1053913
Identification
| Product Name | 17-Amino-10-oxo-3,6,12,15-tetraoxa-9-azaheptadecanoic Acid |
| IUPAC Name | 2-[2-[2-[[2-[2-(2-aminoethoxy)ethoxy]acetyl]amino]ethoxy]ethoxy]acetic acid |
| Molecular Structure |  |
| CAS Registry Number | 1143516-05-5 |
| MDL Number | MFCD13184942 |
| Synonyms | Aeea-aeea 1143516-05-5 17-amino-10-oxo-3,6,12,15-tetraoxa-9-azaheptadecan-1-oic acid 2-[2-[2-[[2-[2-(2-aminoethoxy)ethoxy]acetyl]amino]ethoxy]ethoxy]acetic acid 8-Amino-3,6-dioxaoctanoic acid dimer MFCD13184942 17-Amino-10-oxo-3,6,12,15-tetraoxa-9-azaheptadecanoic acid H-Adoa-Adoa-OH SCHEMBL1257485 AMY3342 YQZVQKYXWPIKIX-UHFFFAOYSA-N DTXSID301191445 EX-A5417 H2N-PEG2-NH-PEG2-CH2COOH ZB0899 AKOS030213455 HY-W125504 AC-32527 SY251169 WS-03066 CS-0183820 P50020 17-amino-10-oxo-3,6,12,15-tetraoxa-9-azaheptadecan-1-oicacid [2-(2-{2-[2-(2-aminoethoxy)ethoxy]acetyl- amino}ethoxy)ethoxy]acetic acid [2-(2-{2-[2-(2-aminoethoxy)ethoxy]acetyl-amino}ethoxy)ethoxy]acetic acid [2-(2-{2-[2-(2-aminoethoxy)ethoxy]acetylamino}ethoxy)ethoxy]acetic acid [2-(2-{2-[2-(2-Aminoethoxyl)ethoxy]acetylamino}ethoxy)ethoxy]acetic acid 2-[2-(2-{2-[2-(2-aminoethoxy)ethoxy]acetamido}ethoxy)ethoxy]acetic acid [2-(2-{2-[2-(2-Amino-ethoxy)-ethoxy]-acetylamino}-ethoxy)-ethoxy]-acetic acid |
| Molecular Formula | C12H24N2O7 |
| Molecular Weight | 308.33 |
| InChI | InChI=1S/C12H24N2O7/c13-1-3-18-5-7-20-9-11(15)14-2-4-19-6-8-21-10-12(16)17/h1-10,13H2,(H,14,15)(H,16,17) |
| InChI Key | YQZVQKYXWPIKIX-UHFFFAOYSA-N |
| Isomeric SMILES | C(COCCOCC(=O)NCCOCCOCC(=O)O)N |
Physical Data
| Appearance | Powder |
Spectra
No data available
Route of Synthesis (ROS)
| Conditions | Yield |
| With N-ethyl-N,N-diisopropylamine In ethanol at 20℃; Experimental Procedure To a solution of 2-(1 9-tert-l3utoxycarbonylnonade- canoylamino)pentanedioic acid 1 -tert-butyl ester 5-(2,5-di- oxopyrrolidin-1-yl) ester (2.50 g) and [2-(2-{2-[2-(2-amino- ethoxy)-ethoxy]acetylamino}ethoxy)ethoxy]acetic acid (alternative name: H-OEG-OEG-OH)(1 .47 g) in ethanol (40 mE) was added DIPEA (1.26 mE). The mixture was stirred at room temperature overnight and then concentrated in vacuo. To the residue was added aqueous 0.1 N HC1 (150 mE) and ethyl acetate (200 mE). The layers were separated and the aqueous layer was extracted with ethyl acetate (100 mE). The combined organic layers were washed with water and brine, dried (magnesium sulphate) and concentrated in vacuo to give an oil, which crystallised on standing. Yield 96% (3.1 g). ECMS: Theoretical mass: 874.2.Found: 874.49. | 96% |
| With N-ethyl-N,N-diisopropylamine In ethanol at 20℃; Experimental Procedure 16.1 Step 1: 19-{(S)-1-tert-Butoxycarbonyl-3-[2-(2-{[2-(2-carboxymethoxy-ethoxy)-ethylcarbamoyl]-methoxy}-ethoxy)-ethylcarbamoyl]-propylcarbamoyl}-nonadecanoic acid tert-butyl ester Step 1: 19-{(S)-1-tert-Butoxycarbonyl-3-[2-(2-{[2-(2-carboxymethoxy-ethoxy)-ethylcarbamoyl]-methoxy}-ethoxy)-ethylcarbamoyl]-propylcarbamoyl}-nonadecanoic acid tert-butyl ester (0556) (0557) To a solution of 2-(19-tert-Butoxycarbonylnonadecanoylamino)pentanedioic acid 1-tert-butyl ester 5-(2,5-dioxopyrrolidin-1-yl) ester (2.50 g, (prepared similarly as described in WO 2005/012347) and [2-(2-{2-[2-(2-Aminoethoxyl)ethoxy]acetylamino}ethoxy)ethoxy]acetic acid (1.47 g, alternative name: ∈-amino-3,6-dioxaoctanoic acid dimer, IRIS Biotech GmbH, Cat. No. PEG1221) in ethanol (40 ml) was added DIPEA (1.26 ml). The mixture was stirred at room temperature over night and then concentrated in vacuo. To the residue was added aqueous 0.1 N HCl (150 ml) and ethyl acetate (200 ml). The layers were separated and the aqueous layer was extracted with ethyl acetate (100 ml). The combined organic layers were washed with water and brine, dried (magnesium sulphate) and concentrated in vacuo to give an oil, which crystallized on standing. Yield 96% (3.1 g). LC-MS (electrospray): m/z=874.49. | 96% |
| With N-ethyl-N,N-diisopropylamine In ethanol at 20℃; | 96% |
Safety and Hazards
No data available
Other Data
| Transportation | Storage at 2~8°, Away from light. |
| Storage | Storage at 2~8°, Away from light. |
| Shelf Life | 1 year |
| Druglikeness | |
| Lipinski rules component | |
| Molecular Weight | 308.332 |
| logP | -2.772 |
| HBA | 9 |
| HBD | 3 |
| Matching Lipinski Rules | 4 |
| Veber rules component | |
| Polar Surface Area (PSA) | 129.34 |
| Rotatable Bond (RotB) | 16 |
| Matching Veber Rules | 1 |
| Use Pattern |
| 17-Amino-10-oxo-3,6,12,15-tetraoxa-9-azaheptadecanoic Acid CAS#: 1143516-05-5 as an intermediate in the synthesis of semaglutide, developing an efficient synthesis route with this intermediate could contribute to the cost-effectiveness of producing semaglutide. |
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