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

HRID 470248Notes

Reaction equation

HRID 470248 reaction equation
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

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-1e2ac775b6364304917e15226371e4db
Source dataset
uspto-grants-2014_01
Patent number
US08629270B2

Reaction notes

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