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Dicyclohexylcarbodiimide → (4S)-3-{[(4-Methoxybenzyl)thio]acetyl}-4-phenyl-1,3-oxazolidin-2-one

HRID 603909
ノート
印刷プレビュー

反応式

HRID 603909 の反応式
[CH3:1][O:2][C:3]1[CH:14]=[CH:13][C:6]([CH2:7][S:8][CH2:9][C:10]([OH:12])=O)=[CH:5][CH:4]=1.C1(N=C=NC2CCCCC2)CCCCC1.[C:30]1([C@H:36]2[CH2:40][O:39][C:38](=[O:41])[NH:37]2)[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1>C(Cl)Cl.CN(C)C1C=CN=CC=1>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:7][S:8][CH2:9][C:10]([N:37]2[C@@H:36]([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)[CH2:40][O:39][C:38]2=[O:41])=[O:12])=[CH:13][CH:14]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

HCID 10868DicyclohexylcarbodiimideHCID 7304242-Oxazolidinone, 4-phenyl-, (4S)-HCID 958072[(4-Methoxybenzyl)sulfanyl]acetic acid

生成物 1

HCID 59326632(4S)-3-{[(4-Methoxybenzyl)thio]acetyl}-4-phenyl-1,3-oxazolidin-2-one

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒
HCID 6344
Dichloromethane
溶媒

実験手順

[(4-Methoxybenzyl)thio]acetic acid (1.3 g, 6.1 mmol) was dissolved in dry CH2Cl2 (40 ml) and given 0° C. N,N′-Dicyclohexylcarbodiimide (DCC, 6.1 g, 6.1 mmol) and 4-(dimethylamino)pyridine (DMAP, 1.6 g, 12.9 mmol) were added and the mixture was stirred for 30 minutes. (S)-(+)-4-Phenyl-2-oxazolidinone (1.0 g, 6.1 mol) was added and the mixture was stirred at room temperature for 24 hours. The mixture was filtrated, concentrated under reduced pressure and purified by flash-chromatography (Hex:EtOAc 8:2 then 1:1). This afforded the title compound.

後処理

  1. customgiven 0° C
  2. stirringthe mixture was stirred at room temperature for 24 hours
  3. filtrationThe mixture was filtrated
  4. concentrationconcentrated under reduced pressure
  5. custompurified by flash-chromatography (Hex

出典と根拠

ORDレコード
ord-398b22afae594e69974a8bf06878a2f2
出典データセット
uspto-grants-2011_03
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07906502B2

反応ノート

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