Sodium Bicarbonate → Racemic Benzyl 2-benzamido-7a-phenyl-4,4a,5,7-tetrahydropyrrolo[3,4-d][1,3]thiazine-6-carboxylate

HRID 470248노트

반응식

HRID 470248 반응식
ClC(N(C)C)=C(C)C.[C:9]([NH:17][C:18]([NH:20][C:21]1([C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)[CH:25]([CH2:26]O)[CH2:24][N:23]([C:28]([O:30][CH2:31][C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)=[O:29])[CH2:22]1)=[S:19])(=[O:16])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.C(=O)([O-])O.[Na+]>ClCCl>[C:9]([NH:17][C:18]1[S:19][CH2:26][CH:25]2[CH2:24][N:23]([C:28]([O:30][CH2:31][C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)=[O:29])[CH2:22][C:21]2([C:38]2[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=2)[N:20]=1)(=[O:16])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

참가 물질

5

반응물 3

HCID 516892Sodium BicarbonateHCID 6407921-Chloro-N,N-2-trimethylpropenylamineHCID 86697917Benzyl 3-(benzoylcarbamothioylamino)-4-(hydroxymethyl)-3-phenyl-pyrrolidine-1-carboxylate

생성물 1

HCID 89832302Racemic Benzyl 2-benzamido-7a-phenyl-4,4a,5,7-tetrahydropyrrolo[3,4-d][1,3]thiazine-6-carboxylate수율 63.2%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

1-Chloro-N,N,2-trimethylpropenylamine (17.9 mL, 135 mmol) is added to a 0° C. solution of racemic benzyl 3-(benzoylcarbamothioylamino)-4-(hydroxymethyl)-3-phenyl-pyrrolidine-1-carboxylate (51 g, 104 mmol) in dichloromethane (459 mL) and stirred at room temperature for 2 hours. A saturated solution of sodium hydrogen carbonate (300 mL) is added and the layers are separated. The organic layer is dried over magnesium sulfate, the solution concentrated. The crude product is purified over silica gel eluting with dichloromethane to 5% ethyl acetate/dichloromethane to give the title compound (31 g, 63%). ES/MS (m/e): 372 (M+H).

후처리

  1. customthe layers are separated
  2. dry with materialThe organic layer is dried over magnesium sulfate
  3. concentrationthe solution concentrated
  4. customThe crude product is purified over silica gel eluting with dichloromethane to 5% ethyl acetate/dichloromethane

출처 및 근거

ORD 기록
ord-1e2ac775b6364304917e15226371e4db
출처 데이터셋
uspto-grants-2014_01
특허 번호
US08629270B2

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