Isobutyl chloroformate → N[(1,1-dimethylethoxy)carbonyl]-2,6-dimethyltyrosyl-N-(3-phenyl propyl)-Nalpha-(2-propenyl)-D-alaninamide

HRID 845899

반응식

HRID 845899 반응식
[CH2:1]([NH:4][C@@H:5]([C:7]([N-:9][CH2:10][CH2:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[O:8])[CH3:6])[CH:2]=[CH2:3].N[C@H](C([N-]CCCC1C=CC=CC=1)=O)C.[C:34]([NH:41][C@H:42]([C:53](O)=[O:54])[CH2:43][C:44]1[C:49]([CH3:50])=[CH:48][C:47]([OH:51])=[CH:46][C:45]=1[CH3:52])([O:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[O:35].C(OC(Cl)=O)C(C)C>C(Cl)Cl.CN(C)C=O>[CH3:40][C:37]([CH3:38])([O:36][C:34]([NH:41][C@H:42]([C:53]([N:4]([CH2:1][CH:2]=[CH2:3])[C@@H:5]([C:7]([NH:9][CH2:10][CH2:11][CH2:12][C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1)=[O:8])[CH3:6])=[O:54])[CH2:43][C:44]1[C:49]([CH3:50])=[CH:48][C:47]([OH:51])=[CH:46][C:45]=1[CH3:52])=[O:35])[CH3:39]

참가 물질

7

반응물 4

HCID 62365Isobutyl chloroformateHCID 13656657(S)-2-tert-Butoxycarbonylamino-3-(4-hydroxy-2,6-dimethyl-phenyl)-propionic acidHCID 178457507N-Allyl-(D)-alanylphenylpropylamideHCID 178462169Alanyl-phenylpropylamide

생성물 1

HCID 10347146N[(1,1-dimethylethoxy)carbonyl]-2,6-dimethyltyrosyl-N-(3-phenyl propyl)-Nalpha-(2-propenyl)-D-alaninamide

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 6344Dichloromethane용매

실험 절차

N-Allyl-(D)-alanylphenylpropylamide (5.00 g, 20.3 mmol) replaced (D) alanyl-phenylpropylamide in the mixed anhydride synthesis described in Example 2. It was reacted using Boc-2,6-dimethyl-tyrosine (6.28 g, 20.3 mmol) N-methyl morpholine (2.05 g, 20.3 mmol) and isobutylchloroformate (2.77 g, 20.3 mmol). Dimethylformamide replaced CH2Cl2 as the solvent. The reaction mixture was worked up as in Example 2 and the resultant oil (10.62 g) was purified by column chromatography on Woelm silica eluting with 3 to 5% methanol-methylene chloride and the diasteromers were separated:

후처리

  1. customIt was reacted
  2. customthe resultant oil (10.62 g) was purified by column chromatography on Woelm silica eluting with 3 to 5% methanol-methylene chloride
  3. customthe diasteromers were separated

출처 및 근거

ORD 기록
ord-889687da4198447f8366425a651885d4
출처 데이터셋
uspto-grants-1988_07
특허 번호
US04760180

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