Lithium Hydroxide → 3-{4-[(E)-3-(3,4-Dichloro-phenyl)-acryloyl]-7-oxo-[1,4]diazepan-1-yl}-propionic acid

HRID 2095478Notes

Reaction equation

HRID 2095478 reaction equation
C([O:3][C:4](=[O:27])[CH2:5][CH2:6][N:7]1[C:13](=[O:14])[CH2:12][CH2:11][N:10]([C:15](=[O:26])/[CH:16]=[CH:17]/[C:18]2[CH:23]=[CH:22][C:21]([Cl:24])=[C:20]([Cl:25])[CH:19]=2)[CH2:9][CH2:8]1)C.[OH-].[Li+].OS([O-])(=O)=O.[K+]>O1CCCC1.C(O)C>[Cl:25][C:20]1[CH:19]=[C:18](/[CH:17]=[CH:16]/[C:15]([N:10]2[CH2:11][CH2:12][C:13](=[O:14])[N:7]([CH2:6][CH2:5][C:4]([OH:27])=[O:3])[CH2:8][CH2:9]2)=[O:26])[CH:23]=[CH:22][C:21]=1[Cl:24]

Participants

5

Reactant 3

HCID 3939Lithium HydroxideHCID 516920Potassium bisulfateHCID 670748533-{4-[(E)-3-(3,4-Dichloro-phenyl)-acryloyl]-7-oxo-[1,4]diazepan-1-yl}-propionic acid ethyl ester

Product 1

HCID 670745383-{4-[(E)-3-(3,4-Dichloro-phenyl)-acryloyl]-7-oxo-[1,4]diazepan-1-yl}-propionic acidYield 98.1%

Reagents, catalysts & solvents 1

HCID 21873804Tetrahydrofuran ethanolSolvent

Procedure

A solution of 3.50 g (8.47 mmol) of 3-{4-[(E)-3-(3,4-dichloro-phenyl)-acryloyl]-7-oxo-[1,4]diazepan-1-yl}-propionic acid ethyl ester in 80 ml of tetrahydrofuran/ethanol (1:1) was treated at 0° C. with 16.94 ml (16.94 mmol) of 1 M aq. lithium hydroxide solution, and kept 3 h at this temperature. The reaction was neutralized with cold aqueous 10% KHSO4 and extracted with EtOAc (3×). The organic phases were washed with aqueous 10% NaCl, dried over Na2SO4 and evaporated to yield 3.20 g (98%) of the titled compound as white solid. MS: 385.0 (MH+, 2Cl).

Workup

  1. extractionextracted with EtOAc (3×)
  2. washThe organic phases were washed with aqueous 10% NaCl
  3. dry with materialdried over Na2SO4
  4. customevaporated

Sources & evidence

ORD record
ord-3b167f0fb29947f388dd990da7e2ffea
Source dataset
uspto-grants-2013_05
Patent number
US08445674B2

Reaction notes

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