Potassium;tri(butan-2-yl)boranuide → tert-Butyl {(3S)-3-{[4-methoxy-3-(3-methoxypropoxy)phenyl]methyl}-4-methyl-1-[(2S,4S)-5-oxo-4-(propan-2-yl)oxolan-2-yl]pentyl}carbamate

HRID 604982Notes

Reaction equation

[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:20][C@H:21]([CH2:25][C:26]1[CH:31]=[CH:30][C:29]([O:32][CH3:33])=[C:28]([O:34][CH2:35][CH2:36][CH2:37][O:38][CH3:39])[CH:27]=1)[CH:22]([CH3:24])[CH3:23])[C:10](=[O:19])[CH2:11][C@@H:12]([CH:16]([CH3:18])[CH3:17])[C:13](O)=[O:14])=[O:7])([CH3:4])([CH3:3])[CH3:2].CCC(C)[BH-](C(C)CC)C(C)CC.[K+]>O1CCCC1>[C:1]([O:5][C:6](=[O:7])[NH:8][C@H:9]([C@@H:10]1[CH2:11][C@@H:12]([CH:16]([CH3:18])[CH3:17])[C:13](=[O:14])[O:19]1)[CH2:20][C@H:21]([CH2:25][C:26]1[CH:31]=[CH:30][C:29]([O:32][CH3:33])=[C:28]([O:34][CH2:35][CH2:36][CH2:37][O:38][CH3:39])[CH:27]=1)[CH:22]([CH3:24])[CH3:23])([CH3:4])([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 30 °C

Procedure

A solution of 5.51 g of (2S,5S,7S)-5-tert-butoxycarbonylamino-2-isopropyl-7-[4-methoxy-3-(3-methoxypropoxy)-benzyl]-8-methyl-4-oxo-nonanoic acid in 25 mL of tetrahydrofuran is cooled to −30° C. and 10 mL of a 1.0 M solution of K-selectride in tetrahydrofuran is added dropwise within 30 minutes. The mixture is stirred for 2 hours at 30° C. and warmed to 0° C. and stirred for 16 hours. The reaction mixture is quenched with 50 mL of 1.0 M hydrochloric acid and extracted three times with 100 mL of dichloromethane. The organic layer is dried and the solvent is removed to give the title compound as a semi solid.

Workup

temperaturewarmed to 0° C.
stirringstirred for 16 hours
customThe reaction mixture is quenched with 50 mL of 1.0 M hydrochloric acid
extractionextracted three times with 100 mL of dichloromethane
customThe organic layer is dried
customthe solvent is removed

Sources & evidence

ORD record: ord-3747794423874b0b80c1145f0598af7b
Source dataset: uspto-grants-2011_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07910774B2

Reaction notes

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