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

HRID 1058770ノート

反応式

HRID 1058770 の反応式
[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]

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

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%).

後処理

  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%)

出典と根拠

ORDレコード
ord-edf37c17871546aebbe58bab8a274b28
出典データセット
uspto-grants-2003_02
特許番号
US06518260B1

反応ノート

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