Sodium Hydroxide → 3-(4-Benzyloxy-2,6-dichloro-benzyl)-2-oxo-1-(4,5,6,7-tetrahydro-3H-benzoimidazol-5-yl)-pyrrolidine-3-carboxylic acid

HRID 1161770Notes

Reaction equation

HRID 1161770 reaction equation
C([O:3][C:4]([C:6]1([CH2:21][C:22]2[C:27]([Cl:28])=[CH:26][C:25]([O:29][CH2:30][C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)=[CH:24][C:23]=2[Cl:37])[CH2:10][CH2:9][N:8]([CH:11]2[CH2:19][CH2:18][C:14]3[N:15]=[CH:16][NH:17][C:13]=3[CH2:12]2)[C:7]1=[O:20])=[O:5])C.[OH-].[Na+]>CO>[CH2:30]([O:29][C:25]1[CH:26]=[C:27]([Cl:28])[C:22]([CH2:21][C:6]2([C:4]([OH:5])=[O:3])[CH2:10][CH2:9][N:8]([CH:11]3[CH2:19][CH2:18][C:14]4[N:15]=[CH:16][NH:17][C:13]=4[CH2:12]3)[C:7]2=[O:20])=[C:23]([Cl:37])[CH:24]=1)[C:31]1[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 686483313-(4-Benzyloxy-2,6-dichloro-benzyl)-2-oxo-1-(4,5,6,7-tetrahydro-3H-benzoimidazol-5-yl)-pyrrolidine-3-carboxylic acid ethyl ester

Product 1

HCID 686483303-(4-Benzyloxy-2,6-dichloro-benzyl)-2-oxo-1-(4,5,6,7-tetrahydro-3H-benzoimidazol-5-yl)-pyrrolidine-3-carboxylic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Dissolve 3-(4-Benzyloxy-2,6-dichloro-benzyl)-2-oxo-1-(4,5,6,7-tetrahydro-3H-benzoimidazol-5-yl)-pyrrolidine-3-carboxylic acid ethyl ester (3 g, 5.5 mmol) (Preparation 11) in 10 ml of Methanol and then add 10 ml of 2N NaOH. Stir this mixture for 16 h, concentrate, and then add dioxane and acetic acid to obtain 3-(4-Benzyloxy-2,6-dichloro-benzyl)-2-oxo-1-(4,5,6,7-tetrahydro-3H-benzoimidazol-5-yl)-pyrrolidine-3-carboxylic acid which is not isolated. Reflux the mixture overnight, quench with water and extract with ethyl acetate. Wash the extracts with saturated bicarbonate and concentrate to 3-(4-Benzyloxy-2,6-dichloro-benzyl)-1-(4,5,6,7-tetrahydro-3H-benzoimidazol-5-yl)-pyrrolidin-2-one product (2.6 g). MS: m/z (M+1)=470.

Workup

  1. concentrationconcentrate

Sources & evidence

ORD record
ord-1657d61c5f964ec5a735ed6e033764a4
Source dataset
uspto-grants-2010_10
Patent number
US07820659B2

Reaction notes

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