Ethyl bromoacetate → Ethyl 3-(4-chlorobenzoylamino)-3-isovalerylpropionate

HRID 485024Notes

Reaction equation

[Cl:1][C:2]1[CH:17]=[CH:16][C:5]([C:6]([NH:8][CH2:9][C:10](=[O:15])[CH2:11][CH:12]([CH3:14])[CH3:13])=[O:7])=[CH:4][CH:3]=1.[H-].[Na+].Br[CH2:21][C:22]([O:24][CH2:25][CH3:26])=[O:23]>>[Cl:1][C:2]1[CH:17]=[CH:16][C:5]([C:6]([NH:8][CH:9]([C:10](=[O:15])[CH2:11][CH:12]([CH3:14])[CH3:13])[CH2:21][C:22]([O:24][CH2:25][CH3:26])=[O:23])=[O:7])=[CH:4][CH:3]=1

Participants

Reactant 3

HCID 7748Ethyl bromoacetate

HCID 24758Sodium hydride

HCID 134903074-Chloro-N-(4-methyl-2-oxopentyl)benzamide

Product 1

HCID 13488803Ethyl 3-(4-chlorobenzoylamino)-3-isovalerylpropionateYield 74.7%

Procedure

2.5 g of N-(4-chlorobenzoyl)isovalerylmethylamine, 0.5 g of 61% sodium hydride and 1.81 g of ethyl bromoacetate are treated in the same manner as described in Preparation 1-(5). 2.5 g of ethyl 3-(4-chlorobenzoylamino)-3-isovalerylpropionate are thereby obtained. Yield: 74.4%.

Workup

customas described in Preparation 1-(5)

Sources & evidence

ORD record: ord-291335a3b1ce4e5d9b8d116e7b2ba796
Source dataset: uspto-grants-1985_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04535089

Reaction notes

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