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

HRID 4764

Reaktionsgleichung

Reaktionsgleichung von HRID 4764
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]

Komponenten

6

Edukt 4

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
-45 °C

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-7d46ffa09cc44e9392e4d49e8eb54422
Quelldatensatz
uspto-grants-1988_02
Patentnummer
US04727189

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