Toluene → (Rac)-4-(3-hydroxy-1-methoxycarbonyl-propyl)-5-oxo-[1,4]diazepane-1-carboxylic acid benzyl ester

HRID 655504Notes

Reaction equation

HRID 655504 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]([O:32][CH3:33])=[O:31])[CH2:20][CH2:21][O:22][Si](C(C)(C)C)(C)C)[CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1(C)C=CC=CC=1.B(Cl)(Cl)Cl>ClCCl>[CH2:1]([O:8][C:9]([N:11]1[CH2:17][CH2:16][C:15](=[O:18])[N:14]([CH:19]([C:30]([O:32][CH3:33])=[O:31])[CH2:20][CH2:21][OH:22])[CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 1140TolueneHCID 25135Boron TrichlorideHCID 67080917(Rac)-4-[3-(tert-butyl-dimethyl-silanyloxy)-1-methoxycarbonyl-propyl]-5-oxo-[1,4]diazepane-1-carboxylic acid benzyl ester

Product 1

HCID 67080666(Rac)-4-(3-hydroxy-1-methoxycarbonyl-propyl)-5-oxo-[1,4]diazepane-1-carboxylic acid benzyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

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 (evaporated twice with toluene) in 25 ml of dichloromethane was treated at 0° C. with 3.20 ml (3.20 mmol, 1 M in dichloromethane) of boron trichloride and kept 1 h at this temperature. The solution was stirred 17 h at room temperature and then extracted with cold sat. aq. sodium hydrogencarbonate solution and ethyl acetate (3×). The organic phases were washed with sat. aq. sodium hydrogencarbonate solution, 10% aq. sodium chloride solution, dried over Na2SO4 evaporated to give 1.34 g (quantitative) of the title compound as yellow viscous oil. MS: 365.1 (MH+).

Workup

  1. extractionextracted with cold sat. aq. sodium hydrogencarbonate solution and ethyl acetate (3×)
  2. washThe organic phases were washed with sat. aq. sodium hydrogencarbonate solution, 10% aq. sodium chloride solution
  3. dry with materialdried over Na2SO4
  4. customevaporated

Sources & evidence

ORD record
ord-1c49bfc10509473da4ccf299d9852c0c
Source dataset
uspto-grants-2011_12
Patent number
US08071586B2

Reaction notes

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