Methyl chloroformate → 1-benzyl 5-tert-butyl (1S)-{1-[(5-amino-1-methyl-1H-pyrazol-4-yl)carbamoyl]pentamethylene}biscarbamate

HRID 459644

반응식

HRID 459644 반응식
[CH2:1]([O:8][C:9]([NH:11][C@@H:12]([CH2:16][CH2:17][CH2:18][CH2:19][NH:20][C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[C:13]([OH:15])=O)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.ClC(OC)=O.S(O)(O)(=O)=O.[CH3:45][N:46]1[C:50]([NH2:51])=[C:49]([NH2:52])[CH:48]=[N:47]1>O1CCCC1.O.C(Cl)(Cl)Cl>[NH2:51][C:50]1[N:46]([CH3:45])[N:47]=[CH:48][C:49]=1[NH:52][C:13]([C@@H:12]([NH:11][C:9](=[O:10])[O:8][CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[CH2:16][CH2:17][CH2:18][CH2:19][NH:20][C:21](=[O:22])[O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:15]

참가 물질

8

반응물 4

HCID 6586Methyl chloroformateHCID 8471Triethylamine2회HCID 98765IN2-(benzyloxycarbonyl)-N6-(tert-butoxycarbonyl)-L-lysineHCID 219045711H-Pyrazole, 4,5-diamine-1-methyl-, sulfate (1:1)

생성물 1

HCID 865978971-benzyl 5-tert-butyl (1S)-{1-[(5-amino-1-methyl-1H-pyrazol-4-yl)carbamoyl]pentamethylene}biscarbamate

시약·촉매·용매 3

HCID 962Water용매HCID 6212Chloroform용매HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of (2S)-2-[(benzyloxycarbonyl)amino]-6-[(tert-butoxycarbonyl)amino]hexanoic acid (19.02 g) and triethylamine (5.56 g) in tetrahydrofuran (200 ml) was added methyl chloroformate (4.21 ml), followed by stirring under ice-cooling for 30 minutes. To the reaction mixture was added a solution of 1-methyl-1H-pyrazole-4,5-diamine sulfate (15.75 g) and triethylamine (15.2 g) in water (50 ml) at the same temperature. The mixture was stirred at room temperature for 30 minutes. To the reaction mixture was added chloroform (300 ml), and the layers were separated. The organic layer was washed successively with 10% aqueous citric acid solution, brine and saturated aqueous sodium hydrogencarbonate solution. The organic layer was dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo to give a crude product of 1-benzyl 5-tert-butyl (1S)-{1-[(5-amino-1-methyl-1H-pyrazol-4-yl)carbamoyl]pentamethylene}biscarbamate as an oil. The crude product was used directly in the next step without further purification.

후처리

  1. temperaturecooling for 30 minutes
  2. stirringThe mixture was stirred at room temperature for 30 minutes
  3. customthe layers were separated
  4. washThe organic layer was washed successively with 10% aqueous citric acid solution, brine and saturated aqueous sodium hydrogencarbonate solution
  5. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-c0874084eb7f46c7bf88e13c69e218d5
출처 데이터셋
uspto-grants-2007_03
특허 번호
US07192943B2

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