N,O-bis(trimethylsilyl)acetamide → Ethyl 2-[[hydroxy[2-phenyl-1-[[(phenylmethoxy)carbonyl]amino]ethyl]phosphinyl]methyl]-4-methylpentanoate

HRID 1058765Notes

Reaction equation

HRID 1058765 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.[CH3:23][CH:24]([CH3:33])[CH2:25][C:26](=[CH2:32])[C:27]([O:29][CH2:30][CH3:31])=[O:28].C/C(/O[Si](C)(C)C)=N\[Si](C)(C)C.C(OCC)(=O)C.O>C(#N)C>[OH:22][P:20]([CH2:32][CH:26]([CH2:25][CH:24]([CH3:23])[CH3:33])[C:27]([O:29][CH2:30][CH3:31])=[O:28])([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)=[O:21]

Participants

6

Reactant 4

HCID 6913588N,O-bis(trimethylsilyl)acetamideHCID 10909818Ethyl 4-methyl-2-methylenepentanoateHCID 22728543Water ethylacetateHCID 178523200HCID 178523200, compound

Product 1

HCID 10528548Ethyl 2-[[hydroxy[2-phenyl-1-[[(phenylmethoxy)carbonyl]amino]ethyl]phosphinyl]methyl]-4-methylpentanoateYield 81.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 1 g (3.13 mmol) of [2-phenyl-1-[[(phenylmethoxy)carbonyl]amino]ethyl]phosphinic acid synthesized in 1.4., 2.2 g (14.10 mmol) of ethyl 4-methyl-2-methylenepentanoate 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 and the combined organic phases are washed with water, dried over sodium sulphate, filtered and evaporated under vacuum. The product is purified by recrystallization from a mixture of ethyl acetate and hexane. 1.21 g of product are recovered (yield=81.3%).

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 under vacuum
  6. customThe product is purified by recrystallization from a mixture of ethyl acetate and hexane
  7. custom1.21 g of product are recovered (yield=81.3%)

Sources & evidence

ORD record
ord-1c38c02e40824d8681cb259986f97b98
Source dataset
uspto-grants-2003_02
Patent number
US06518260B1

Reaction notes

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