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

HRID 342284

反応式

HRID 342284 の反応式
[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]

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 241Benzene溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-4e0b1971d8f14a3cae8d4741d6dd1082
出典データセット
uspto-grants-1999_01
特許番号
US05856556

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