Potassium Cyanide → (2S,9S)-2-[(tert-Butoxycarbonyl)amino]-7-(carbobenzyloxy)-10-cyano-9-hydroxy-7-azadecanoic Acid tert-Butyl Ester

HRID 1068076Notes

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)([CH3:4])([CH3:3])[CH3:2].[C-:37]#[N:38].[K+].C1OCCOCCOCCOCCOCCOC1>>[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][C:37]#[N:38])([CH3:4])([CH3:3])[CH3:2]

Participants

Reactant 3

HCID 9032Potassium Cyanide

HCID 2855718-Crown-6

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

Product 1

HCID 10577855(2S,9S)-2-[(tert-Butoxycarbonyl)amino]-7-(carbobenzyloxy)-10-cyano-9-hydroxy-7-azadecanoic Acid tert-Butyl EsterYield 51.1%

Procedure

According to the method described for the preparation of 14a, 13b (3.23 g, 6.10 mmol) was reacted with KCN (3.96 g, 60.82 mmol) and 18-crown-6 (242 mg, 0.92 mmol) to obtain 14b (1.62 g, 51%) as a colorless oil: 1H NMR δ 1.20-1.84 (m, 6H), 1.44 (s, 9H), 1.45 (s, 9H), 2.55 (m, 2H), 3.20-3.50 (m, 4H), 3.92 (dd, 1H, J=8.2, 5.1), 4.07 (m, 1H), 5.13 (s, 2H), 7.26-7.41 (m, 5H); 13C NMR δ 24.1, 24.2, 28.3, 28.8, 32.4, 55.7, 67.1, 68.4, 80.4, 82.5, 118.9, 129.0, 129.2, 129.6, 138.0, 158.1, 173.7; HRMS m/z calcd for C27H42N3O7 520.3023, found 520.3048. Anal. calcd. for C27H41N3O7: C 62.41, H 7.95, N 8.09. Found: C 62.14, H 7.95, N 7.97. [α]22D−5.3 (c 1.15, CH3OH).

Sources & evidence

ORD record: ord-ae574e6e457b49619f6a6ba5f3a3947f
Source dataset: uspto-grants-2001_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06248866B1

Reaction notes

Loading…