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

HRID 1170605노트

반응식

HRID 1170605 반응식
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]

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 6344Dichloromethane용매

실험 절차

To a solution of 2,2-dimethyl propionic acid 4-methoxybenzyl 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.

후처리

  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

출처 및 근거

ORD 기록
ord-b3765bc538794954a21de455f699249c
출처 데이터셋
uspto-grants-2010_11
특허 번호
US07825238B2

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