2,4,5-Trichlorophenol → Benzyloxycarbonyl-D-phenylalanine 2,4,5-trichlorophenyl ester

HRID 256330노트

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HRID 256330 반응식
[CH2:1]([O:8][C:9]([NH:11][C@@H:12]([C:20]([OH:22])=[O:21])[CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl:23][C:24]1[CH:29]=[C:28]([Cl:30])[C:27]([Cl:31])=[CH:26][C:25]=1O.C1(N=C=NC2CCCCC2)CCCCC1>O1CCCC1>[Cl:23][C:24]1[CH:29]=[C:28]([Cl:30])[C:27]([Cl:31])=[CH:26][C:25]=1[O:21][C:20](=[O:22])[C@@H:12]([CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[NH:11][C:9]([O:8][CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)=[O:10]

참가 물질

5

반응물 3

HCID 72712,4,5-TrichlorophenolHCID 10868DicyclohexylcarbodiimideHCID 675678N-(Benzyloxycarbonyl)-D-phenylalanine

생성물 1

HCID 14632444Benzyloxycarbonyl-D-phenylalanine 2,4,5-trichlorophenyl ester

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

60.0 g (0.2 mole) of benzyloxycarbonyl-D-phenylalanine [H. Yajima and K. Kubo: J. Am. Chem. Soc. 87, 2039-2044 (1965)] and 39.4 g (0.2 mole) of 2,4,5-trichlorophenol are dissolved in 200 ml of tetrahydrofuran, the solution is cooled to 5° to 10° C., then at stirring 41.2 g (0.2 mole) of dicyclohexylcarbodiimide are added in about 30 minutes. The reaction mixture is stirred for 6 hours without refrigeration. The precipitated dicyclohexylurea is filtered, washed three times with 50 ml of tetrahydrofuran and the combined tetrahydrofurane solutions are evaporated at reduced pressure. The residue is crystallized from 300 ml of hot etanol, filtered, washed twice with 50 ml of ethanol having a temperature of 5° to 10° C., then the crystals are dried in a vacuum desiccator. Yield: 72 g (75%).

후처리

  1. temperaturethe solution is cooled to 5° to 10° C.
  2. additionare added in about 30 minutes
  3. filtrationThe precipitated dicyclohexylurea is filtered
  4. washwashed three times with 50 ml of tetrahydrofuran
  5. customthe combined tetrahydrofurane solutions are evaporated at reduced pressure
  6. customThe residue is crystallized from 300 ml of hot etanol
  7. filtrationfiltered
  8. washwashed twice with 50 ml of ethanol having a temperature of 5° to 10° C.
  9. customthe crystals are dried in a vacuum desiccator

출처 및 근거

ORD 기록
ord-4db6dc43eb604d35946c71886863256e
출처 데이터셋
uspto-grants-1987_10
특허 번호
US04703036

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