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5-[2-[(Butylamino)carbonyl]-3-methyl-1-butenyl]-4-(cyclohexylmethyl)-2,2-dimethyl-3-oxazolidinecarboxylic acid, 1,1-dimethylethyl ester → 5-[2-[(Butylamino)carbonyl]-3-methylbutyl]-4-(cyclohexylmethyl)-2,2-dimethyl-3-oxazolidinecarboxylic acid, 1,1-dimethylethyl ester

HRID 1941349
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HRID 1941349 반응식
[CH2:1]([NH:5][C:6]([C:8]([CH:31]([CH3:33])[CH3:32])=[CH:9][CH:10]1[O:14][C:13]([CH3:16])([CH3:15])[N:12]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH:11]1[CH2:24][CH:25]1[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]1)=[O:7])[CH2:2][CH2:3][CH3:4]>C1COCC1.C(Cl)(Cl)Cl.[Rh]>[CH2:1]([NH:5][C:6]([CH:8]([CH:31]([CH3:32])[CH3:33])[CH2:9][CH:10]1[O:14][C:13]([CH3:15])([CH3:16])[N:12]([C:17]([O:19][C:20]([CH3:21])([CH3:22])[CH3:23])=[O:18])[CH:11]1[CH2:24][CH:25]1[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]1)=[O:7])[CH2:2][CH2:3][CH3:4]
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참가 물질

5

반응물 1

HCID 867517825-[2-[(Butylamino)carbonyl]-3-methyl-1-butenyl]-4-(cyclohexylmethyl)-2,2-dimethyl-3-oxazolidinecarboxylic acid, 1,1-dimethylethyl ester

생성물 1

HCID 147770545-[2-[(Butylamino)carbonyl]-3-methylbutyl]-4-(cyclohexylmethyl)-2,2-dimethyl-3-oxazolidinecarboxylic acid, 1,1-dimethylethyl ester수율 71.8%

시약·촉매·용매 3

HCID 23948Rhodium촉매2회HCID 6212Chloroform용매
HCID 8028
Tetrahydrofuran
용매
2회

실험 절차

A THF (2.03 mL) solution containing 5-[2-[(butylamino)carbonyl]-3-methyl-1-butenyl]-4-(cyclohexylmethyl)-2,2-dimethyl-3-oxazolidinecarboxylic acid, 1,1-dimethylethyl ester (236 mg, 0.51 mmol) and rhodium on alumina (24 mg, 10% by wt, 5% Rh content) was placed under a hydrogen atmosphere for 16 h. Additional rhodium on alumina (24 mg) in THF (2.03 mL) was added and the reaction continued under H2 atmosphere for 6 h. The mixture was diluted with CHCl3, filtered and concentrated in vacuo. Silica gel chromatography (3:1 to 3:2 hexane:Et2O gradient) of the concentrate afforded the title compound (171 mg, 70%). MS (ESI) m/e 465 (M-H)-MS (ESI) m/e 467 (M+H)+.

후처리

  1. waitthe reaction continued under H2 atmosphere for 6 h
  2. filtrationfiltered
  3. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-a5b2b051d4cb4003a9471f1a78220a8e
출처 데이터셋
uspto-grants-1997_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05703129

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