Triethylamine → (2S,9R)-2-[(tert-Butoxycarbonyl)amino]-7-(carbobenzyloxy)-10-chloro-9-hydroxy-7-azadecanoic Acid tert-Butyl Ester

HRID 1068075Notes

Reaction equation

HRID 1068075 reaction equation
[C:1]([O:5][C:6](=[O:36])[C@@H:7]([NH:28][C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])[CH2:8][CH2:9][CH2:10][CH2:11][N:12]([C:18]([O:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=[O:19])[CH2:13][C@H:14]([OH:17])[CH2:15][Cl:16])([CH3:4])([CH3:3])[CH3:2].C(OC(=O)[C@@H](NC(OC(C)(C)C)=O)CCCCNC[C@@H](O)CCl)(C)(C)C.ClC(OCC1C=CC=CC=1)=O.C(N(CC)CC)C>>[C:1]([O:5][C:6](=[O:36])[C@@H:7]([NH:28][C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])[CH2:8][CH2:9][CH2:10][CH2:11][N:12]([C:18]([O:20][CH2:21][C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1)=[O:19])[CH2:13][C@@H:14]([OH:17])[CH2:15][Cl:16])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 4

HCID 8471TriethylamineHCID 10387Benzyl chloroformateHCID 10548694(2S,9R)-2-[(tert-Butoxycarbonyl)amino]-10-chloro-9-hydroxy-7-azadecanoic Acid tert-Butyl EsterHCID 10792289(2S,9S)-2-[(tert-Butoxycarbonyl)amino]-7-(carbobenzyloxy)-10-chloro-9-hydroxy-7-azadecanoic Acid tert-Butyl Ester

Product 1

HCID 11800320(2S,9R)-2-[(tert-Butoxycarbonyl)amino]-7-(carbobenzyloxy)-10-chloro-9-hydroxy-7-azadecanoic Acid tert-Butyl EsterYield 85%

Procedure

According to the method described for the preparation of 13a, 12b (2.93 g, 7.42 mmol) was reacted with benzyl chloroformate (1.60 g, 9.38 mmol) and triethylamine (1.50 g, 14.81 mmol) to obtain 13b (3.35 g, 85%) as a colorless oil: 1H NMR δ 1.24-1.82 (m, 6H), 1.44 (s, 9H) 1.45 (s, 9H), 3.15-3.64 (m, 6H), 3.92 (m, 1H), 4.00 (m, 1H), 5.12 (m, 2H), 7.25-7.40 (m, 5H); 13C NMR δ 24.0, 28.3, 28.8, 32.5, 42.4, 51.3, 52.3, 55.7, 68.4, 71.0, 71.1, 80.4, 82.5, 129.0, 129.1, 129.6, 138.0, 158.1, 158.4, 173.7; HRMS m/z calcd for C26H42ClN2O7 529.2681, found 529.2691. Anal. calcd. for C26H41ClN2O7: C 59.03, H 7.81, N 5.29. Found: C 58.88, H 7.83, N 5.23. [α]23D−1.7°(c 0.98, CH3OH).

Sources & evidence

ORD record
ord-a55b3faf10f644658769f49b06cc9689
Source dataset
uspto-grants-2001_06
Patent number
US06248866B1

Reaction notes

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