Triethylamine → Tert-butyl trans-4-(N-methoxy-N-methylcarbamoyl)cyclohexylcarbamate

HRID 29758

반응식

HRID 29758 반응식
[C:1]([O:5][C:6]([NH:8][CH:9]1[CH2:14][CH2:13][CH:12]([C:15]([OH:17])=O)[CH2:11][CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:18][O:19][NH:20][CH3:21].C1CCC(N=C=NC2CCCCC2)CC1.C(N(CC)CC)C>CN(C=O)C.O>[C:1]([O:5][C:6](=[O:7])[NH:8][CH:9]1[CH2:10][CH2:11][CH:12]([C:15](=[O:17])[N:20]([O:19][CH3:18])[CH3:21])[CH2:13][CH2:14]1)([CH3:2])([CH3:3])[CH3:4]

참가 물질

7

반응물 4

HCID 8471TriethylamineHCID 10868DicyclohexylcarbodiimideHCID 14232N,O-DimethylhydroxylamineHCID 27559964-(((Tert-butoxy)carbonyl)amino)cyclohexane-1-carboxylic acid

생성물 1

HCID 24720928Tert-butyl trans-4-(N-methoxy-N-methylcarbamoyl)cyclohexylcarbamate수율 61%

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

실험 절차

A solution of 4-[N-(tert-butoxycarbonyl)amino]-cyclohexane carboxylic acid (11.95 g, 49.0 mmol), O,N-dimethylhydroxylamine (4.88 g, 50.0 mmol), DCC (9.60 g, 50 mmol) and triethylamine (5.06 g, 50.0 mmol) in DMF (150 mL) was stirred at room temperature overnight. Water (500 mL) was added and the mixture was extracted with CHCl3. The organic phase was washed with water, dried and concentrated under reduced pressure. Purification by flash chromatography (hexane/EtOAc 1:1) gave [4-(methoxy-methyl-carbamoyl)-cyclohexyl]-carbamic acid tert-butyl ester (8.50 g, 61%).

후처리

  1. extractionthe mixture was extracted with CHCl3
  2. washThe organic phase was washed with water
  3. customdried
  4. concentrationconcentrated under reduced pressure
  5. customPurification by flash chromatography (hexane/EtOAc 1:1)

출처 및 근거

ORD 기록
ord-c7af7f81ca4e42c0a273fa448c39b0b8
출처 데이터셋
uspto-grants-2008_09
특허 번호
US07423012B2

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