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

HRID 2230405노트

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HRID 2230405 반응식
[CH2:1]([O:8][C:9]([NH:11][C@H:12]([C:17]([NH:19][C@@H:20]([CH2:41][OH:42])[C@@H:21]([OH:40])[C@@H:22]([OH:39])[C@H:23]([OH:38])[C:24]([NH:26][C@H:27]([C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)[CH2:28][C:29]([OH:31])=[O:30])=[O:25])=[O:18])[CH2:13][CH:14]([CH3:16])[CH3:15])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N12CCCN=C1CCCCC2.[C:54]([O:60][CH2:61]I)(=[O:59])[C:55]([CH3:58])([CH3:57])[CH3:56].O>CN(C)C=O>[CH2:1]([O:8][C:9]([NH:11][C@H:12]([C:17]([NH:19][C@@H:20]([CH2:41][OH:42])[C@@H:21]([OH:40])[C@@H:22]([OH:39])[C@H:23]([OH:38])[C:24]([NH:26][C@H:27]([C:32]1[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=1)[CH2:28][C:29]([O:31][CH2:61][O:60][C:54](=[O:59])[C:55]([CH3:58])([CH3:57])[CH3:56])=[O:30])=[O:25])=[O:18])[CH2:13][CH:14]([CH3:15])[CH3:16])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

참가 물질

6

반응물 4

HCID 962WaterHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 104401Iodomethyl pivalateHCID 59902690(S)-3-[(2S,3R,4R,5S)-5-(N-benzyloxycarbonyl-L-leucyl)amino-2,3,4,6-tetrahydroxyhexanoyl]amino-3-phenylpropionic acid

생성물 1

HCID 53899016pivaloyloxymethyl (S)-3-[(2S,3R,4R,5S)-5-(N-benzyloxycarbonyl-L-leucyl)amino-2,3,4,6-tetrahydroxyhexanoyl]amino-3-phenylpropionate수율 45.4%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매2회

실험 절차

To a solution of (S)-3-[(2S,3R,4R,5S)-5-(N-benzyloxycarbonyl-L-leucyl)amino-2,3,4,6-tetrahydroxyhexanoyl]amino-3-phenylpropionic acid (295 mg) and 1,8-diazabicyclo[5.4.0]undec-7-ene (0.082 ml) in dimethylformamide (2 ml) was added a solution of iodomethyl pivalate (139 mg) in dimethylformamide (1 ml) and the mixture was stirred at room temperature for 1 hour. After addition of water, the reaction mixture was extracted with ethyl acetate and the extract was washed with 10% aqueous citric acid solution, saturated aqueous sodium hydrogencarbonate solution andsaturated brine respectively. The organic solution was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was passed through a column of silica gel, followed by elution with ethyl acetate:methanol (10:1). The effective fractions were combined and concentrated under reduced pressure. Recrystallization from chloroform provided the title compound (160 mg).

후처리

  1. extractionthe reaction mixture was extracted with ethyl acetate
  2. washthe extract was washed with 10% aqueous citric acid solution, saturated aqueous sodium hydrogencarbonate solution
  3. dry with materialThe organic solution was dried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. washfollowed by elution with ethyl acetate:methanol (10:1)
  6. concentrationconcentrated under reduced pressure
  7. customRecrystallization from chloroform

출처 및 근거

ORD 기록
ord-15cf3e091ff847f88b58a0d9ce74d3f4
출처 데이터셋
uspto-grants-2002_07
특허 번호
US06423869B1

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