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

HRID 2230403노트

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HRID 2230403 반응식
Cl.[OH:2][C@@H:3]([C@H:18]([OH:33])[C@H:19]([OH:32])[C@@H:20]([NH:23][C:24](=[O:31])[C@H:25]([CH2:27][CH:28]([CH3:30])[CH3:29])[NH2:26])[CH2:21][OH:22])[C:4]([NH:6][C@H:7]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[CH2:8][C:9]([OH:11])=[O:10])=[O:5].[C:34]1([C:40]([C:43]2[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=2)=[N+]=[N-])[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1.C(=O)([O-])O.[Na+].Cl[C:55]([O:57][CH2:58][C:59]1[CH:64]=[CH:63][CH:62]=[CH:61][CH:60]=1)=[O:56]>CO.O>[CH2:58]([O:57][C:55]([NH:26][C@H:25]([C:24]([NH:23][C@@H:20]([CH2:21][OH:22])[C@@H:19]([OH:32])[C@@H:18]([OH:33])[C@H:3]([OH:2])[C:4]([NH:6][C@H:7]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[CH2:8][C:9]([O:11][CH:40]([C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1)[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)=[O:10])=[O:5])=[O:31])[CH2:27][CH:28]([CH3:29])[CH3:30])=[O:56])[C:59]1[CH:64]=[CH:63][CH:62]=[CH:61][CH:60]=1

참가 물질

7

반응물 4

HCID 10387Benzyl chloroformateHCID 612301,1'-(Diazomethylene)bis(benzene)HCID 516892Sodium BicarbonateHCID 69823761(S)-3-[(2S,3R,4R,5S)-2,3,4,6-tetrahydroxy-5-(L-leucyl)aminohexanoyl]amino-3-phenylpropionic acid hydrochloride

생성물 1

HCID 59902693diphenylmethyl (S)-3-[(2S,3R,4R,5S)-5-(N-benzyloxycarbonyl-L-leucyl)amino-2,3,4,6-tetrahydroxyhexanoyl]amino-3-phenylpropionate

시약·촉매·용매 2

HCID 887Methanol용매2회HCID 962Water용매

실험 절차

To a solution of (S)-3-[(2S,3R,4R,5S)-2,3,4,6-tetrahydroxy-5-(L-leucyl)aminohexanoyl]amino-3-phenylpropionic acid hydrochloride (4.35 g) in methanol (100 ml) was added a solution of diphenyldiazomethane (3.40 g) in methanol (100 ml) under ice-cooling and the mixture was stirred at room temperature for 15 hours. Removal of the organic solvent gave a residue, which was suspended in water (200 ml). To the suspension were added sodium hydrogencarbonate (2.20 g) and benzyl chloroformate (18 ml) and the mixture was stirred at room temperature for 2 hours. The reaction mixture was extracted with ethyl acetate and the extract was washed with saturated brine. The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was recrystallized from ethyl acetate to give the title compound (5.95 g).

후처리

  1. temperaturecooling
  2. customRemoval of the organic solvent
  3. customgave a residue, which
  4. stirringthe mixture was stirred at room temperature for 2 hours
  5. extractionThe reaction mixture was extracted with ethyl acetate
  6. washthe extract was washed with saturated brine
  7. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was recrystallized from ethyl acetate

출처 및 근거

ORD 기록
ord-60b024f9d5514479995a54a6382c7a32
출처 데이터셋
uspto-grants-2002_07
특허 번호
US06423869B1

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