Methyl 2-benzylprop-2-enoate → Methyl alpha-[[hydroxy[1-[[(phenylmethoxy)carbonyl]amino]ethyl]phosphinyl]methyl]benzenepropanoate

HRID 1058770Notes

Reaction equation

HRID 1058770 reaction equation
[PH2:1](=[O:3])[OH:2].[C:4]1([CH2:10][C:11](=[CH2:16])[C:12]([O:14][CH3:15])=[O:13])[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[CH3:17]/[C:18](/O[Si](C)(C)C)=[N:19]\[Si](C)(C)C.[C:29]([O:32][CH2:33][CH3:34])(=[O:31])C.O>C(#N)C>[OH:3][P:1]([CH2:16][CH:11]([CH2:10][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)[C:12]([O:14][CH3:15])=[O:13])([CH:18]([NH:19][C:29]([O:32][CH2:33][C:34]1[CH:8]=[CH:9][CH:4]=[CH:5][CH:6]=1)=[O:31])[CH3:17])=[O:2]

Participants

6

Reactant 4

HCID 575761Methyl 2-benzylprop-2-enoateHCID 4124402Phosphinic AcidHCID 6913588N,O-bis(trimethylsilyl)acetamideHCID 22728543Water ethylacetate

Product 1

HCID 18668704Methyl alpha-[[hydroxy[1-[[(phenylmethoxy)carbonyl]amino]ethyl]phosphinyl]methyl]benzenepropanoateYield 68.9%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 0.6 g (2.47 mmol) of 1-[[(phenylmethoxy)carbonyl]amino]ethyl]phosphinic acid, 2.17 g (12.3 mmol) of methyl 2-(phenylmethyl)propenoate and 0.52 ml of N,O-bis(trimethylsilyl)acetamide in 0.27 ml of acetonitrile is stirred at a temperature in the region of 20° C. for 24 hours. 60 ml of a 1/1 ethyl acetate/water mixture are added. The aqueous phase is extracted with ethyl acetate. The combined organic phases are washed with water, dried over sodium sulphate, filtered and evaporated off under vacuum. The product is purified by recrystallization from a mixture of ethyl acetate and hexane. 0.71 g of product are recovered (yield=68.9%).

Workup

  1. extractionThe aqueous phase is extracted with ethyl acetate
  2. washThe combined organic phases are washed with water
  3. dry with materialdried over sodium sulphate
  4. filtrationfiltered
  5. customevaporated off under vacuum
  6. customThe product is purified by recrystallization from a mixture of ethyl acetate and hexane
  7. custom0.71 g of product are recovered (yield=68.9%)

Sources & evidence

ORD record
ord-edf37c17871546aebbe58bab8a274b28
Source dataset
uspto-grants-2003_02
Patent number
US06518260B1

Reaction notes

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