HuagongsheHuagongshe Chemistry Print Report · For research reference only
(2S,9S)-2-[(tert-Butoxycarbonyl)amino]-7-(carbobenzyloxy)-10-cyano-9-hydroxy-7-azadecanoic Acid tert-Butyl Ester → (2S,9S)-2-[(tert-Butoxycarbonyl)amino]-11-amino-9-hydroxy-7-azaundecanoic Acid tert-Butyl Ester, Diacetate Salt
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | (2S,9S)-2-[(tert-Butoxycarbonyl)amino]-7-(carbobenzyloxy)-10-cyano-9-hydroxy-7-azadecanoic Acid tert-Butyl Ester | HCID 10577855 | — |
| Reactant | (2S, 9R)-2-[(tert-Butoxycarbonyl)amino]-11-amino-9-hydroxy-7-azaundecanoic Acid tert-Butyl Ester, Diacetate Salt | HCID 131721417 | — |
| Catalyst | Palladium | HCID 23938 | — |
| Catalyst | Adams' catalyst | HCID 345198 | — |
| Solvent | Acetic Acid | HCID 176 | — |
| Product | (2S,9S)-2-[(tert-Butoxycarbonyl)amino]-11-amino-9-hydroxy-7-azaundecanoic Acid tert-Butyl Ester, Diacetate Salt | HCID 131722679 | — |
Reaction Steps
According to the method described for the preparation of 15a, to a solution of 14b (172 mg, 0.33 mmol) in glacial acetic acid (5 mL) was added 10% Pd—C (17 mg) and PtO2 (35 mg) under an H2 atmosphere to obtain 15b in quantitative yield as a colorless oil: 1H NMR (D2O) δ 1.30-2.00 (m, 8H), 1.45 (s, 9H), 1.48 (s, 9H), 1.92 (s, 6H), 2.99-3.28 (m, 6H), 3.99 (dd, 1H, J=9.0, 5.11), 4.06 (it, 1H, J=9.5, 3.3); HRMS m/z calcd for C19H40N3O5 390.2968, found 390.2967. [α]22D−7.5° (c 1.03, CH3OH).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US06248866B1 |
| Source dataset | uspto-grants-2001_06 |
| ORD ID | ord-c59f9e8c560146a39001db3b50e019dc |
| Source note | uspto-grants-2001_06 |