Ammonia → N-[(Benzyloxy)carbonyl]-L-isoleucyl-L-prolyl-L-prolinamide

HRID 1282960노트

반응식

HRID 1282960 반응식
[CH2:1]([O:8][C:9]([NH:11][C@H:12]([C:17]([N:19]1[CH2:33][CH2:32][CH2:31][C@H:20]1[C:21]([N:23]1[CH2:30][CH2:29][CH2:28][C@H:24]1[C:25]([OH:27])=O)=[O:22])=[O:18])[C@H:13]([CH2:15][CH3:16])[CH3:14])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.ClC(OCC(C)C)=O.[NH3:42]>O1CCCC1.C(N(CC)CC)C>[CH2:1]([O:8][C:9]([NH:11][C@H:12]([C:17]([N:19]1[CH2:33][CH2:32][CH2:31][C@H:20]1[C:21]([N:23]1[CH2:30][CH2:29][CH2:28][C@H:24]1[C:25]([NH2:42])=[O:27])=[O:22])=[O:18])[C@H:13]([CH2:15][CH3:16])[CH3:14])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

참가 물질

6

반응물 3

HCID 222AmmoniaHCID 62365Isobutyl chloroformateHCID 54515815N-[(Benzyloxy)carbonyl]-L-isoleucyl-L-prolyl-L-proline

생성물 1

HCID 53756909N-[(Benzyloxy)carbonyl]-L-isoleucyl-L-prolyl-L-prolinamide

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 8471Triethylamine용매

실험 절차

Benzyloxycarbonyl-isoleucyl-prolyl-proline (4.5 g) is dissolved in a mixture of tetrahydrofuran (30 ml) and triethylamine (1.4 ml). The solution is chilled in a -5° cooling bath and isobutyl chloroformate (1.6 ml) is added. The solution is allowed to warm to room temperature (10 minutes) and concentrated aqueous ammonia (10 ml) is added. After four hours stirring at room temperature, the reaction is concentrated in vacuo, diluted with ethyl acetate and washed sequentially with saturated sodium bicarbonate, water, 0.1 N hydrochloric acid and water. The organic phase is dried over magnesium sulfate and concentrated to dryness in vacuo to give the title compound.

후처리

  1. temperatureThe solution is chilled in a -5°
  2. temperaturecooling bath
  3. additionis added
  4. concentrationthe reaction is concentrated in vacuo
  5. additiondiluted with ethyl acetate
  6. washwashed sequentially with saturated sodium bicarbonate, water, 0.1 N hydrochloric acid and water
  7. dry with materialThe organic phase is dried over magnesium sulfate
  8. concentrationconcentrated to dryness in vacuo

출처 및 근거

ORD 기록
ord-ba999c62b81b408e83dcc33283325721
출처 데이터셋
uspto-grants-1976_08
특허 번호
US03973006

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