1-Chloro-N,N-2-trimethylpropenylamine → Racemic Benzyl 2-benzamido-7a-(2-thienyl)-4,4a,5,7-tetrahydropyrrolo[3,4-d][1,3]thiazine-6-carboxylate

HRID 470249Notes

Reaction equation

[C:1]([NH:9][C:10]([NH:12][C:13]1([C:30]2[S:31][CH:32]=[CH:33][CH:34]=2)[CH:17]([CH2:18]O)[CH2:16][N:15]([C:20]([O:22][CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[O:21])[CH2:14]1)=[S:11])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.ClC(N(C)C)=C(C)C>C(Cl)Cl>[C:1]([NH:9][C:10]1[S:11][CH2:18][CH:17]2[CH2:16][N:15]([C:20]([O:22][CH2:23][C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)=[O:21])[CH2:14][C:13]2([C:30]2[S:31][CH:32]=[CH:33][CH:34]=2)[N:12]=1)(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a 0° C. solution of racemic benzyl 3-(benzoylcarbamothioylamino)-4-(hydroxymethyl)-3-(2-thienyl)pyrrolidine-1-carboxylate (30 g, 60.5 mmol) in methylene chloride (300 mL) is added a methylene chloride solution (20 mL) of 1-chloro-N,N,2-trimethylpropenylamine (9.61 mL, 72.6 mmol). The resulting solution is stirred at 0° C. for 30 minutes and then warmed to room temperature. The solution is quenched with saturated sodium bicarbonate solution, the organic layer is isolated, dried over sodium sulfate and concentrated. The crude mixture is purified over silica gel eluting with 5% to 50% ethyl acetate in hexanes gradient to give the title compound (24 g, 83%). ES/MS (m/e): 478 (M+H).

Workup

temperaturewarmed to room temperature
customThe solution is quenched with saturated sodium bicarbonate solution
customthe organic layer is isolated
dry with materialdried over sodium sulfate
concentrationconcentrated
customThe crude mixture is purified over silica gel eluting with 5% to 50% ethyl acetate in hexanes gradient

Sources & evidence

ORD record: ord-0c755ad5673c471eb2f07b5ea83b73e5
Source dataset: uspto-grants-2014_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08629270B2

Reaction notes

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