Dicyclohexylcarbodiimide → 2,2-dimethyl-3-(N-CBz-D-valyloxy)-propionic acid

HRID 989951

反応式

HRID 989951 の反応式
COC1C=CC(C[O:8][C:9](=[O:14])[C:10]([CH3:13])([CH3:12])[CH3:11])=CC=1.[C:17]([NH:27][C@@H:28]([C:32]([OH:34])=[O:33])[CH:29]([CH3:31])[CH3:30])([O:19][CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[O:18].C1CCC(N=C=NC2CCCCC2)CC1>ClCCl.CN(C)C1C=CN=CC=1>[CH3:11][C:10]([CH3:13])([CH2:12][O:33][C:32](=[O:34])[C@@H:28]([CH:29]([CH3:30])[CH3:31])[NH:27][C:17]([O:19][CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[O:18])[C:9]([OH:14])=[O:8]

参加物

6

反応物 3

HCID 10868DicyclohexylcarbodiimideHCID 5780012,2-Dimethylpropionic acid, 4-methoxybenzyl esterHCID 712434N-alpha-Benzyloxycarbonyl-D-valine

生成物 1

HCID 233874902,2-dimethyl-3-(N-CBz-D-valyloxy)-propionic acid

試薬・触媒・溶媒 2

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

実験手順

To a solution of 2,2-dimethyl propionic acid 4methoxybenzyl ester (4.7 g, 20 mmole) and N-CBz-D-valine (5.5 g, 22 mmole) in dichloromethane (100 ml) were added 4-dimethyaminopyridine (305 mg, 2.5 mmole) and DCC (5.15 g, 25 mmole). After 18 hr, the solution was washed successively with sodium bicarbonate aqueous solution, citric acid solution and water. The organic phase was dried and the residue was dissolved in dichloromethane (100 ml). To the solution was added trifluoroacetic acid (10 ml). After 3 hr, it was evaporated and the product was isolated with silica gel column chromatography. 4.5 g. The compound may be activated and esterified to a drug or further modified as described below.

後処理

  1. washthe solution was washed successively with sodium bicarbonate aqueous solution, citric acid solution and water
  2. customThe organic phase was dried
  3. dissolutionthe residue was dissolved in dichloromethane (100 ml)
  4. additionTo the solution was added trifluoroacetic acid (10 ml)
  5. waitAfter 3 hr
  6. customit was evaporated
  7. customthe product was isolated with silica gel column chromatography

出典と根拠

ORDレコード
ord-bddafb0ffba743bca7524df11985465c
出典データセット
uspto-grants-2002_10
特許番号
US06458772B1

関連ノート

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