Dichloromethane → N-[(1,1-dimethylethoxy)carbonyl]-2,6-dimethyl-tyrosyl-N-(3-phenylpropyl)-D-alaninamide

HRID 745489

반응식

HRID 745489 반응식
C(Cl)Cl.[CH3:4][C:5]([CH3:30])([O:7][C:8]([NH:10][C@H:11]([C:22]([NH:24][C@@H:25]([C:27]([OH:29])=O)[CH3:26])=[O:23])[CH2:12][C:13]1[C:18]([CH3:19])=[CH:17][C:16]([OH:20])=[CH:15][C:14]=1[CH3:21])=[O:9])[CH3:6].CN1CCOCC1.[C:38]1([CH2:44][CH2:45][CH2:46][NH2:47])[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1>CCOC(C)=O>[CH3:4][C:5]([CH3:6])([O:7][C:8]([NH:10][C@H:11]([C:22]([NH:24][C@@H:25]([C:27]([NH:47][CH2:46][CH2:45][CH2:44][C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1)=[O:29])[CH3:26])=[O:23])[CH2:12][C:13]1[C:18]([CH3:19])=[CH:17][C:16]([OH:20])=[CH:15][C:14]=1[CH3:21])=[O:9])[CH3:30]

참가 물질

6

반응물 4

HCID 6344DichloromethaneHCID 79724-MethylmorpholineHCID 162593-PhenylpropylamineHCID 13656701N-[(1,1-dimethylethoxy)carbonyl]-2,6-dimethyl-tyrosyl-D-alanine

생성물 1

HCID 13656661N-[(1,1-dimethylethoxy)carbonyl]-2,6-dimethyl-tyrosyl-N-(3-phenylpropyl)-D-alaninamide

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매

반응 조건

온도
-45 °C

실험 절차

A CH2Cl2 solution (100 ml) of the title compound from Example 9, (16.6 g, 43.6 mmole) was charged with 4.4 g (43.6 mmoles) of NMM and cooled to -45° C. To this solution was added 5.7 g (43.6 mmole) of IBCF and the mixture warmed to 10° C. The solution was then cooled to -25° C. before adding 7.4 g (54.5 mmole) of 3-phenylpropylamine. After allowing the reaction to warm to room temperature and stand overnight, it was diluted with 300 ml of EtOAc and extracted with three 100 ml portions of 0.5N KHSO4. The combined aqueous washes were extracted with 100 ml of EtOAc and this extract was combined with the original organic phase. The combined organic was then washed with one 150 ml portion of brine before drying it over Na2SO4. All solvent was removed under reduced pressure to give the title product as a foam. This material was chromatographed to give 10 g (46%) of a compound identical to diastereomer S of Example 3.

후처리

  1. additionTo this solution was added 5.7 g (43.6 mmole) of IBCF
  2. temperaturethe mixture warmed to 10° C
  3. temperatureThe solution was then cooled to -25° C.
  4. customthe reaction
  5. temperatureto warm to room temperature
  6. extractionextracted with three 100 ml portions of 0.5N KHSO4
  7. extractionThe combined aqueous washes were extracted with 100 ml of EtOAc
  8. washThe combined organic was then washed with one 150 ml portion of brine
  9. dry with materialbefore drying it over Na2SO4
  10. customAll solvent was removed under reduced pressure

출처 및 근거

ORD 기록
ord-a5a704d2b25b424392bf9a7f996afb23
출처 데이터셋
uspto-grants-1986_07
특허 번호
US04599325

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