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

HRID 899060

反応式

HRID 899060 の反応式
[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]

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

実験手順

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%).

後処理

  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)

出典と根拠

ORDレコード
ord-04a1777065d14d92a4cdde19c8fed3d1
出典データセット
uspto-grants-2008_04
特許番号
US07354895B1

関連ノート

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