(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

HRID 1068077Notes

Reaction equation

HRID 1068077 reaction equation
[C:1]([OH:4])(=[O:3])[CH3:2].[C:5]([OH:8])(=[O:7])[CH3:6].[C:9]([O:13][C:14](=[O:35])[C@@H:15]([NH:27][C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[CH2:16][CH2:17][CH2:18][CH2:19][NH:20][CH2:21][C@H:22]([OH:26])[CH2:23][CH2:24][NH2:25])([CH3:12])([CH3:11])[CH3:10].C(OC(=O)[C@@H](NC(OC(C)(C)C)=O)CCCCN(C(OCC1C=CC=CC=1)=O)C[C@@H](O)CC#N)(C)(C)C>C(O)(=O)C.[Pd].O=[Pt]=O>[C:1]([OH:4])(=[O:3])[CH3:2].[C:5]([OH:8])(=[O:7])[CH3:6].[C:9]([O:13][C:14](=[O:35])[C@@H:15]([NH:27][C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[CH2:16][CH2:17][CH2:18][CH2:19][NH:20][CH2:21][C@@H:22]([OH:26])[CH2:23][CH2:24][NH2:25])([CH3:12])([CH3:11])[CH3:10]

Participants

6

Reactant 2

HCID 10577855(2S,9S)-2-[(tert-Butoxycarbonyl)amino]-7-(carbobenzyloxy)-10-cyano-9-hydroxy-7-azadecanoic Acid tert-Butyl EsterHCID 131721417(2S, 9R)-2-[(tert-Butoxycarbonyl)amino]-11-amino-9-hydroxy-7-azaundecanoic Acid tert-Butyl Ester, Diacetate Salt

Product 1

HCID 131722679(2S,9S)-2-[(tert-Butoxycarbonyl)amino]-11-amino-9-hydroxy-7-azaundecanoic Acid tert-Butyl Ester, Diacetate Salt

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 345198Adams' catalystCatalystHCID 176Acetic AcidSolvent

Procedure

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).

Sources & evidence

ORD record
ord-c59f9e8c560146a39001db3b50e019dc
Source dataset
uspto-grants-2001_06
Patent number
US06248866B1

Reaction notes

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