Dicyclohexylcarbodiimide → 4-methoxybenzyl 4(2-N-benzyloxycarbonyl-L-valyloxyethoxy)benzoate

HRID 489055노트

반응식

HRID 489055 반응식
[OH:1][CH2:2][CH2:3][O:4][C:5]1[CH:22]=[CH:21][C:8]([C:9]([O:11][CH2:12][C:13]2[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=2)=[O:10])=[CH:7][CH:6]=1.[CH2:23]([O:30][C:31]([NH:33][C@H:34]([C:38](O)=[O:39])[CH:35]([CH3:37])[CH3:36])=[O:32])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.C1(N=C=NC2CCCCC2)CCCCC1>CN(C)C1C=CN=CC=1.ClCCl>[CH2:23]([O:30][C:31]([NH:33][C@H:34]([C:38]([O:1][CH2:2][CH2:3][O:4][C:5]1[CH:6]=[CH:7][C:8]([C:9]([O:11][CH2:12][C:13]2[CH:14]=[CH:15][C:16]([O:19][CH3:20])=[CH:17][CH:18]=2)=[O:10])=[CH:21][CH:22]=1)=[O:39])[CH:35]([CH3:37])[CH3:36])=[O:32])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

참가 물질

6

반응물 3

HCID 10868DicyclohexylcarbodiimideHCID 726987N-Carbobenzoxy-L-valineHCID 220358874-Methoxybenzyl 4-(2-hydroxyethoxy)benzoate

생성물 1

HCID 233875454-methoxybenzyl 4(2-N-benzyloxycarbonyl-L-valyloxyethoxy)benzoate

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 6344Dichloromethane용매

실험 절차

To a solution of 4-methoxybenzyl 4-(2-hydroxyethoxy)benzoate (6.6 g, 21.8 mmole), 4-dimethylaminopyridine (0.61 g, 5 mmole) and N-benzyloxycarbonyl-L-valine (6.3 g, 25 mmole) in dichloromethane (80 ml) was added dicyclohexyl-carbodiimide (5.2 g, 25 mmole) and the mixture was stirred overnight at room temperature. The mixture was cooled and the urethane was filtered. The solution was evaporated and ethyl acetate (200 ml) was added. The organic phase was washed twice with 5% acetic acid, 5% sodium hydrogencarbonate and water. The organic phase was dried with sodium sulfate and evaporated under reduced pressure. The product was isolated by silica gel column chromatography with dichloromethane/methanol. Yield: 10.6 g=90%

후처리

  1. temperatureThe mixture was cooled
  2. filtrationthe urethane was filtered
  3. customThe solution was evaporated
  4. additionethyl acetate (200 ml) was added
  5. washThe organic phase was washed twice with 5% acetic acid, 5% sodium hydrogencarbonate and water
  6. dry with materialThe organic phase was dried with sodium sulfate
  7. customevaporated under reduced pressure
  8. customThe product was isolated by silica gel column chromatography with dichloromethane/methanol

출처 및 근거

ORD 기록
ord-ff54fcdfd2fa43cfaab33331239946f6
출처 데이터셋
uspto-grants-2005_12
특허 번호
US06974802B2

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