m-Chloroperbenzoic acid → tert-Butyl {(1S)-1-[(2R)-oxiran-2-yl]-2-phenylethyl}carbamate

HRID 263756ノート

反応式

HRID 263756 の反応式
ClC1C=CC=C(C(OO)=[O:9])C=1.[C:12]([NH:19][C@H:20]([CH:28]=[CH2:29])[CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13]>C(Cl)Cl>[C:12]([NH:19][C@H:20]([C@@H:28]1[CH2:29][O:9]1)[CH2:21][C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1)([O:14][C:15]([CH3:17])([CH3:16])[CH3:18])=[O:13]

参加物

4

反応物 2

HCID 70297m-Chloroperbenzoic acidHCID 11064740(S)-tert-Butyl 1-phenylbut-3-en-2-ylcarbamate

生成物 1

HCID 9813904tert-Butyl {(1S)-1-[(2R)-oxiran-2-yl]-2-phenylethyl}carbamate

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

A solution of 9.74 g of m-chloroperbenzoic acid in 50 ml of methylene chloride is added over the course of 15 min at from 0° to 5° C. to a solution of 1.45 g of N-Boc-1-phenyl-3-buten-2(S)-amine in 20 ml of methylene chloride. The batch is stirred for 18 h at that same temperature and is then stirred for a further 8 h, with heating to RT, to complete the reaction and poured onto ice-cold 10% sodium carbonate solution. The aqueous phase is extracted three times with ether. The combined organic phases are washed in succession three times with 10% sodium sulfite solution, three times with saturated sodium hydrogen carbonate solution, with sodium thiosulfate solution and with brine and dried over sodium sulfate. After concentrating the solvents, the title compound is purified by column chromatography (SiO2, hexane/ethyl acetate: 4/1) and recrystallised from hexane. M.p. 51°-52° C.; TLC Rf (C)=0.33; FAB-MS (M+H)+=264.

後処理

  1. stirringis then stirred for a further 8 h
  2. customthe reaction
  3. additionpoured onto ice-cold 10% sodium carbonate solution
  4. extractionThe aqueous phase is extracted three times with ether
  5. washThe combined organic phases are washed in succession three times with 10% sodium sulfite solution, three times with saturated sodium hydrogen carbonate solution, with sodium thiosulfate solution and with brine
  6. dry with materialdried over sodium sulfate
  7. concentrationAfter concentrating the solvents
  8. customthe title compound is purified by column chromatography (SiO2, hexane/ethyl acetate: 4/1)
  9. customrecrystallised from hexane

出典と根拠

ORDレコード
ord-83cec1ecf4cd4c9ea71659d9998b833b
出典データセット
uspto-grants-1997_07
特許番号
US05643878

反応ノート

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