Dicyclohexylcarbodiimide → Benzyl 5-(N-FMOC-L-valyloxy)-4-hydroxy-2-pentenoate

HRID 989996

반응식

HRID 989996 반응식
[OH:1][CH:2]([CH2:15][OH:16])[CH:3]=[CH:4][C:5]([O:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)=[O:6].[C:17]([NH:34][C@H:35]([C:39](O)=[O:40])[CH:36]([CH3:38])[CH3:37])([O:19][CH2:20][CH:21]1[C:33]2[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=2)[C:27]2[C:22]1=[CH:23][CH:24]=[CH:25][CH:26]=2)=[O:18].C1CCC(N=C=NC2CCCCC2)CC1>CN(C1C=CN=CC=1)C.ClCCl>[C:17]([NH:34][C@H:35]([C:39]([O:16][CH2:15][CH:2]([OH:1])[CH:3]=[CH:4][C:5]([O:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)=[O:6])=[O:40])[CH:36]([CH3:37])[CH3:38])([O:19][CH2:20][CH:21]1[C:33]2[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=2)[C:27]2[C:22]1=[CH:23][CH:24]=[CH:25][CH:26]=2)=[O:18]

참가 물질

6

반응물 3

HCID 10868DicyclohexylcarbodiimideHCID 688217FMOC-L-valineHCID 54529065Benzyl 4,5-dihydroxy-2-pentenoate

생성물 1

HCID 54039988Benzyl 5-(N-FMOC-L-valyloxy)-4-hydroxy-2-pentenoate

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 6344Dichloromethane용매2회

반응 조건

온도
10 °C

실험 절차

A mixture of benzyl 4,5-dihydroxy-2-pentenoate (4.4 g, 20 mmole), N-FMOC-L-valine (5.8 g, 17 mmole) and DMAP (0.21 g, 1.7 mmole) in 100 ml dichloromethane was cooled to about 10° C. A solution of DCC (4.2 g, 20 mmole) in 25 ml dichloromethane was added dropwise at the same temperature and the mixture was stirred overnight at room temperature. The mixture was cooled to 5° C. and the urethane was filtered. The filtrate was evaporated under reduced pressure and the product was isolated by silica gel column chromatography. Yield: 6.6 g=71%

후처리

  1. temperatureThe mixture was cooled to 5° C.
  2. filtrationthe urethane was filtered
  3. customThe filtrate was evaporated under reduced pressure
  4. customthe product was isolated by silica gel column chromatography

출처 및 근거

ORD 기록
ord-89a89f6a177147aba1c45018eb0c03db
출처 데이터셋
uspto-grants-2002_10
특허 번호
US06458772B1

연결된 노트

불러오는 중…