Dicyclohexylcarbodiimide → (3S, 4R)3-[(R)-1-t-Butyldimethylsilyloxyethyl]-4-([2-(p-nitrobenzyloxycarbonylamino)ethylthio]carbonyl-methyl)-2-azetidinone

HRID 342284

반응식

HRID 342284 반응식
[Si:1]([O:8][C@@H:9]([C@@H:11]1[C@@H:14]([CH2:15][C:16]([OH:18])=O)[NH:13][C:12]1=[O:19])[CH3:10])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[N+:20]([C:23]1[CH:36]=[CH:35][C:26]([CH2:27][O:28][C:29]([NH:31][CH2:32][CH2:33][SH:34])=[O:30])=[CH:25][CH:24]=1)([O-:22])=[O:21].C1(N=C=NC2CCCCC2)CCCCC1>C1C=CC=CC=1.CN(C)C1C=CN=CC=1>[Si:1]([O:8][C@@H:9]([C@@H:11]1[C@@H:14]([CH2:15][C:16]([S:34][CH2:33][CH2:32][NH:31][C:29]([O:28][CH2:27][C:26]2[CH:35]=[CH:36][C:23]([N+:20]([O-:22])=[O:21])=[CH:24][CH:25]=2)=[O:30])=[O:18])[NH:13][C:12]1=[O:19])[CH3:10])([C:4]([CH3:5])([CH3:6])[CH3:7])([CH3:2])[CH3:3]

참가 물질

6

반응물 3

HCID 10868DicyclohexylcarbodiimideHCID 3017625(4-Nitrophenyl)methyl (2-mercaptoethyl)carbamateHCID 10859145(3S,4R)-3-[(1R)-1-t-butyldimethylsilyloxyethyl]-4-carboxymethyl-2-oxoazetidine

생성물 1

HCID 13219828(3S, 4R)3-[(R)-1-t-Butyldimethylsilyloxyethyl]-4-([2-(p-nitrobenzyloxycarbonylamino)ethylthio]carbonyl-methyl)-2-azetidinone수율 87%

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 241Benzene용매

실험 절차

1.00 9 (3,48 mmole) of (3S, 4R)-3-[(R)-1-t-butyldimethylsilyloxyethyl]-4-carboxymethyl-2-azetidinone and 1.07 g (4.8 mmole) of 2-(p-nitrobenzyloxycarbonyl-amino)ethanethiol were dissolved in 20 ml of benzene. To this solution were added 861 mg (4.18 mmole) of dicyclohexylcarbodiimide and 10 mg (0.082 mmole) of 4-dimethylaminopyridine, at room temperature with stirring. The mixture was stirred for 2 hours, after which the insolubles which had formed were filtered off and the resulting filtrate was concentrated to dryness by evaporation under reduced pressure, The residue was purified by column chromatography through 40 g of silica gel, to give 1.59 g (yield 87%) of the desired product as an oil from the fractions eluted with a 1:1 volume mixture of benzene and ethyl acetate.

후처리

  1. stirringThe mixture was stirred for 2 hours
  2. customafter which the insolubles which had formed
  3. filtrationwere filtered off
  4. concentrationthe resulting filtrate was concentrated to dryness by evaporation under reduced pressure
  5. customThe residue was purified by column chromatography through 40 g of silica gel

출처 및 근거

ORD 기록
ord-4e0b1971d8f14a3cae8d4741d6dd1082
출처 데이터셋
uspto-grants-1999_01
특허 번호
US05856556

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