Benzyl chloroformate → (S)-3-[(2S,3R,4R,5S)-5-(N-benzyloxycarbonyl-L-leucyl)amino-2,3,4,6-tetrahydroxyhexanoyl]amino-3-phenylpropionic acid

HRID 2230402노트

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HRID 2230402 반응식
[OH:1][C@@H:2]([C@H:17]([OH:32])[C@H:18]([OH:31])[C@@H:19]([NH:22][C:23](=[O:30])[C@H:24]([CH2:26][CH:27]([CH3:29])[CH3:28])[NH2:25])[CH2:20][OH:21])[C:3]([NH:5][C@H:6]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[CH2:7][C:8]([OH:10])=[O:9])=[O:4].[OH-].[Na+].Cl[C:36]([O:38][CH2:39][C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1)=[O:37]>>[CH2:39]([O:38][C:36]([NH:25][C@H:24]([C:23]([NH:22][C@@H:19]([CH2:20][OH:21])[C@@H:18]([OH:31])[C@@H:17]([OH:32])[C@H:2]([OH:1])[C:3]([NH:5][C@H:6]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[CH2:7][C:8]([OH:10])=[O:9])=[O:4])=[O:30])[CH2:26][CH:27]([CH3:28])[CH3:29])=[O:37])[C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1

참가 물질

4

반응물 3

HCID 10387Benzyl chloroformateHCID 14798Sodium Hydroxide2회HCID 10456696(S)-3-[(2S,3R,4R,5S)-2,3,4,6-tetrahydroxy-5-(L-leucyl)aminohexanoyl]amino-3-phenylpropionic acid2회

생성물 1

HCID 59902690(S)-3-[(2S,3R,4R,5S)-5-(N-benzyloxycarbonyl-L-leucyl)amino-2,3,4,6-tetrahydroxyhexanoyl]amino-3-phenylpropionic acid

실험 절차

To a mixture of (S)-3-[(2S,3R,4R,5S)-2,3,4,6-tetrahydroxy-5-(L-leucyl)aminohexanoyl]amino-3-phenylpropionic acid (Compound 3) (2.28 g) and 0.2N aqueous sodium hydroxide solution (25 ml) were added benzyl chloroformate (0.714 ml) and 1N aqueous sodium hydroxide solution at 0° C. After stirring at room temperature for 3 hours, the mixture was washed with diethylether and acidified with 1N hydrochloric acid (20 ml). The aqueous solution was extracted with ethyl acetate and the organic layer was washed with saturated brine and dried over anhydrous sodium sulfate. Removal of the organic solvent gave a residue, which was recrystallized from diethylether-hexane to afford the title compound(1.51 g)

후처리

  1. washthe mixture was washed with diethylether
  2. extractionThe aqueous solution was extracted with ethyl acetate
  3. washthe organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customRemoval of the organic solvent
  6. customgave a residue, which
  7. customwas recrystallized from diethylether-hexane

출처 및 근거

ORD 기록
ord-b61b399701ba4eb19085546c20912de0
출처 데이터셋
uspto-grants-2002_07
특허 번호
US06423869B1

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