Ethyl bromoacetate → Ethyl 3-(4-fluorobenzoylamino)-3-isobutyrylpropionate

HRID 485022Notes

Reaction equation

[F:1][C:2]1[CH:16]=[CH:15][C:5]([C:6]([NH:8][CH2:9][C:10](=[O:14])[CH:11]([CH3:13])[CH3:12])=[O:7])=[CH:4][CH:3]=1.[H-].[Na+].Br[CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22]>>[F:1][C:2]1[CH:16]=[CH:15][C:5]([C:6]([NH:8][CH:9]([C:10](=[O:14])[CH:11]([CH3:13])[CH3:12])[CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22])=[O:7])=[CH:4][CH:3]=1

Participants

Reactant 3

HCID 7748Ethyl bromoacetate

HCID 24758Sodium hydride

HCID 13490306N-(4-fluorobenzoyl)isobutyrylmethylamine

Product 1

HCID 14269213Ethyl 3-(4-fluorobenzoylamino)-3-isobutyrylpropionateYield 90.2%

Procedure

5.6 g of N-(4-fluorobenzoyl)isobutyrylmethylamine, 1.2 g of 61% sodium hydride and 4.61 g of ethyl bromoacetate are treated in the same manner as described in Preparation 1-(5). 7.0 g of ethyl 3-(4-fluorobenzoylamino)-3-isobutyrylpropionate are thereby obtained as oil. Yield: 90.0%

Workup

customas described in Preparation 1-(5)

Sources & evidence

ORD record: ord-67a04e1fce9945a1aa1d9b8298dab316
Source dataset: uspto-grants-1985_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04535089

Reaction notes

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