Methyl 2-benzylprop-2-enoate → Methyl 3-[hydroxy[2-phenyl-1-[[(phenylmethoxy)carbonyl)amino]ethyl]phosphinyl]-2-(phenylmethyl)propanoate

HRID 1058759Notes

Reaction equation

HRID 1058759 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.[CH2:23]=[C:24]([CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[C:25]([O:27][CH3:28])=[O:26].C/C(/O[Si](C)(C)C)=N\[Si](C)(C)C>C(OCC)(=O)C.O>[OH:22][P:20]([CH:8]([NH:9][C:10]([O:12][CH2:13][C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1)=[O:11])[CH2:7][C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)([CH2:23][CH:24]([CH2:29][C:30]1[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=1)[C:25]([O:27][CH3:28])=[O:26])=[O:21]

Participants

5

Reactant 3

HCID 575761Methyl 2-benzylprop-2-enoateHCID 6913588N,O-bis(trimethylsilyl)acetamideHCID 178523200HCID 178523200, compound

Product 1

HCID 18668709Methyl 3-[hydroxy[2-phenyl-1-[[(phenylmethoxy)carbonyl)amino]ethyl]phosphinyl]-2-(phenylmethyl)propanoateYield 67%

Reagents, catalysts & solvents 1

HCID 22728543Water ethylacetateSolvent

Procedure

A solution of 1 g (3.31 mmol) of [2-phenyl-1-[[(phenylmethoxy)carbonyl]amino]ethyl]phosphinic acid, 0.66 g (3.75 mmol) of methyl α-methylenebenzenepropanoate and 3.1 ml of N,O-bis(trimethylsilyl)acetamide is maintained at 60° C. for 24 hours. After cooling, 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 under vacuum. The residue is purified by recrystallization from a mixture of ethyl acetate and hexane. 1.04 g of product are recovered (yield=67%).

Workup

  1. temperatureAfter cooling
  2. extractionThe aqueous phase is extracted with ethyl acetate
  3. washThe combined organic phases are washed with water
  4. dry with materialdried over sodium sulphate
  5. filtrationfiltered
  6. customevaporated under vacuum
  7. customThe residue is purified by recrystallization from a mixture of ethyl acetate and hexane
  8. custom1.04 g of product are recovered (yield=67%)

Sources & evidence

ORD record
ord-10c79680e9874e4a8e26863ccc2de203
Source dataset
uspto-grants-2003_02
Patent number
US06518260B1

Reaction notes

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