Potassium bisulfate → (Rac)-4-[3-(tert-butyl-dimethyl-silanyloxy)-1-hydroxymethyl-propyl]-5-oxo-[1,4]diazepane-1-carboxylic acid benzyl ester

HRID 655506Notes

Reaction equation

[CH2:1]([O:8][C:9]([N:11]1[CH2:17][CH2:16][C:15](=[O:18])[N:14]([CH:19]([C:30](OC)=[O:31])[CH2:20][CH2:21][O:22][Si:23]([C:26]([CH3:29])([CH3:28])[CH3:27])([CH3:25])[CH3:24])[CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[BH4-].[Li+].S([O-])(O)(=O)=O.[K+]>C(O)C>[CH2:1]([O:8][C:9]([N:11]1[CH2:17][CH2:16][C:15](=[O:18])[N:14]([CH:19]([CH2:30][OH:31])[CH2:20][CH2:21][O:22][Si:23]([C:26]([CH3:27])([CH3:29])[CH3:28])([CH3:25])[CH3:24])[CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of 1.53 g (3.20 mmol) of (rac)-4-[3-(tert-butyl-dimethyl-silanyloxy)-1-methoxycarbonyl-propyl]-5-oxo-[1,4]diazepane-1-carboxylic acid benzyl ester (intermediate 5A) in 32 ml of ethanol was treated at 0° C. with 0.14 g (6.40 mmol) of lithium borohydride. The reaction was stirred 10 min at 0° C. and 1.5 h at room temperature, then neutralized with cold 10% aq. potassium hydrogensulfate solution and extracted with diethyl ether (3×). The organic phases were washed with 10% aq. potassium hydrogensulfate solution, 10% aq. sodium chloride solution, dried over Na2SO4 evaporated to yield 1.29 g (89%) of the title compound as light yellow viscous oil. MS: 451.2 (MH+).

Workup

extractionextracted with diethyl ether (3×)
washThe organic phases were washed with 10% aq. potassium hydrogensulfate solution, 10% aq. sodium chloride solution
dry with materialdried over Na2SO4
customevaporated

Sources & evidence

ORD record: ord-4946d25387684911a74750a26ad32bfe
Source dataset: uspto-grants-2011_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08071586B2

Reaction notes

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