Ethyl 2-(4-bromobenzyl)acrylate → Ethyl 3-(4-bromophenyl)-2-[[hydroxy[2-phenyl-1-[[(phenyl-methoxy)carbonyl]amino]ethyl]phosphinyl]methyl]propanoate

HRID 1058767Notes

Reaction equation

HRID 1058767 reaction equation
[C:1]1([CH2:7][CH:8]([PH:20](=[O:22])[OH:21])[NH:9][C:10]([O:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[O:11])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Br:23][C:24]1[CH:29]=[CH:28][C:27]([CH2:30][C:31](=[CH2:37])[C:32]([O:34][CH2:35][CH3:36])=[O:33])=[CH:26][CH:25]=1>>[Br:23][C:24]1[CH:25]=[CH:26][C:27]([CH2:30][CH:31]([CH2:37][P:20]([OH:21])([CH:8]([NH:9][C:10]([O:12][CH2:13][C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)=[O:11])[CH2:7][C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)=[O:22])[C:32]([O:34][CH2:35][CH3:36])=[O:33])=[CH:28][CH:29]=1

Participants

3

Reactant 2

HCID 12026123Ethyl 2-(4-bromobenzyl)acrylateHCID 178523200HCID 178523200, compound

Product 1

HCID 18668696Ethyl 3-(4-bromophenyl)-2-[[hydroxy[2-phenyl-1-[[(phenyl-methoxy)carbonyl]amino]ethyl]phosphinyl]methyl]propanoateYield 84.1%

Procedure

The process is performed according to the operating conditions described in 1.6., starting with 2 g (6.27 mmol) of [2-phenyl-1-[(phenylmethoxy)carbonyl]aminoethyl]phosphinic acid synthesized in 1.4. and 2 g (7.44 mol) of ethyl 4-bromo-α-methylenebenzenepropanoate. 3.1 g of product are recovered (yield=84.1%)

Workup

  1. customsynthesized in 1.4
  2. custom3.1 g of product are recovered (yield=84.1%)

Sources & evidence

ORD record
ord-f5c1b9d5a2d642c59aef6f18812a274d
Source dataset
uspto-grants-2003_02
Patent number
US06518260B1

Reaction notes

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