Potassium Carbonate → N-[1(S)-Ethoxycarbonyl-3-phenylpropyl]-L-alanine

HRID 345186

반응식

HRID 345186 반응식
[CH2:1]([NH:3][C@H:4]([C:13]([OH:15])=[O:14])[CH2:5][CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[CH3:2].[C:16]1(C)C(S(O[C@H](C)C(OCC2C=CC=CC=2)=O)(=O)=O)=CC=C[CH:21]=1.[C:39](=[O:42])([O-])[O-:40].[K+].[K+]>C(#N)C>[CH2:16]([O:14][C:13]([C@@H:4]([NH:3][C@H:1]([C:39]([OH:40])=[O:42])[CH3:2])[CH2:5][CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)=[O:15])[CH3:21]

참가 물질

5

반응물 3

HCID 11430Potassium CarbonateHCID 18647272(2S)-2-(ethylamino)-4-phenylbutanoic acidHCID 86745135benzyl (R)-alpha-toluenesulfonyloxypropionate

생성물 1

HCID 5702571N-[1(S)-Ethoxycarbonyl-3-phenylpropyl]-L-alanine

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

Ethyl (S)-homophenylalanine (I') and benzyl (R)-α-toluenesulfonyloxypropionate (II') in the presence or absence of potassium carbonate were added to acetonitrile (15 ml, bp 82° C.), and refluxed for a predetermined time, while stirring. After completing the reaction, the mixture was concentrated under reduced pressure and water (10 ml) was added to the oily residue. Then the mixture was extracted with toluene (10 ml). The organic layer was concentrated under reduced pressure to remove toluene. The oily residue was subjected to silica gel column chromatography to give the compound N-[(lS)-1-ethoxycarbonyl-3-phenylpropyl]-L-alanine. The reaction conditions are shown in Table 3.

후처리

  1. temperaturerefluxed for a predetermined time
  2. customthe reaction
  3. concentrationthe mixture was concentrated under reduced pressure and water (10 ml)
  4. additionwas added to the oily residue
  5. extractionThen the mixture was extracted with toluene (10 ml)
  6. concentrationThe organic layer was concentrated under reduced pressure
  7. customto remove toluene

출처 및 근거

ORD 기록
ord-a514b0037b054f80bd8b3b0a39c51b65
출처 데이터셋
uspto-grants-1991_10
특허 번호
US05055588

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