Dicyclohexylcarbodiimide → (4S)-3-({[(5,5-Dimethyl-2-phenyl-1,3-dioxan-2-yl)methyl]thio}acetyl)-4-phenyl-1,3-oxazolidin-2-one

HRID 254083

반응식

HRID 254083 반응식
[CH3:1][C:2]1([CH3:20])[CH2:7][O:6][C:5]([CH2:14][S:15][CH2:16][C:17]([OH:19])=O)([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[O:4][CH2:3]1.C1(N=C=NC2CCCCC2)CCCCC1.[C:36]1([C@H:42]2[CH2:46][O:45][C:44](=[O:47])[NH:43]2)[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1>C(Cl)Cl.CN(C)C1C=CN=CC=1>[CH3:20][C:2]1([CH3:1])[CH2:3][O:4][C:5]([CH2:14][S:15][CH2:16][C:17]([N:43]2[C@@H:42]([C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=3)[CH2:46][O:45][C:44]2=[O:47])=[O:19])([C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)[O:6][CH2:7]1

참가 물질

6

반응물 3

HCID 10868DicyclohexylcarbodiimideHCID 7304242-Oxazolidinone, 4-phenyl-, (4S)-HCID 66843086{[(5,5-Dimethyl-2-phenyl-1,3-dioxan-2-yl)methyl]thio}acetic acid

생성물 1

HCID 66842977(4S)-3-({[(5,5-Dimethyl-2-phenyl-1,3-dioxan-2-yl)methyl]thio}acetyl)-4-phenyl-1,3-oxazolidin-2-one

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 6344Dichloromethane용매

반응 조건

온도
0 °C

실험 절차

{[(5,5-Dimethyl-2-phenyl-1,3-dioxan-2-yl)methyl]thio}acetic acid (9.9 g, 33.0 mmol) was dissolved in dry CH2Cl2 (250 ml) and cooled to 0° C. N,N′-Dicyclohexylcarbodiimide (DCC, 7.63 g, 37.0 mmol) and 4-(dimethylamino)pyridine (DMAP, 8.57 g, 70.0 mmol) were added and the mixture was stirred at 0° C. for 20 minutes. (S)-(+)-4-Phenyl-2-oxazolidinone (5.38 g, 33.0 mmol) was added and the mixture was stirred at room temperature for 70 h. The mixture was filtered, concentrated under reduced pressure and purified by flash-chromatography (hexane:EtOAc-7:3). This afforded 10.2 g (70%) of the title compound as a white solid. 1H-NMR (CDCl3, 200 MHz): 0.6 (s, 3H), 1.3 (s, 3H), 2.8 (s, 2H), 3.4 (s, 4H), 3.8 (s, 2H), 4.1-4.15 (dd, 1H), 4.6-4.8 (t, 1H), 5.35-5.45 (dd, 1H), 7.25-7.45 (m, 9H).

후처리

  1. stirringthe mixture was stirred at room temperature for 70 h
  2. filtrationThe mixture was filtered
  3. concentrationconcentrated under reduced pressure
  4. custompurified by flash-chromatography (hexane:EtOAc-7:3)

출처 및 근거

ORD 기록
ord-ad76ef6b39c14ff992e47ee0d53923cf
출처 데이터셋
uspto-grants-2011_01
특허 번호
US07871998B2

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