Racemic tert-Butyl-2-benzamido-7a-phenyl-4,4a,5,7-tetrahydropyrrolo[3,4-d][1,3]thiazine-6-carboxylate → tert-Butyl (4aR,7aS)-2-(benzoylamino)-7a-phenyl-4a,5,7,7a-tetrahydropyrrolo[3,4-d][1,3]thiazine-6(4H)-carboxylate

HRID 338119Notes

Reaction equation

HRID 338119 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:16][CH:15]2[C:10]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)([N:11]=[C:12]([NH:17][C:18](=[O:25])[C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[S:13][CH2:14]2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>C(O)C.C(Cl)(Cl)Cl>[C:18]([NH:17][C:12]1[S:13][CH2:14][C@@H:15]2[CH2:16][N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[CH2:9][C@:10]2([C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=2)[N:11]=1)(=[O:25])[C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1

Participants

3

Reactant 1

HCID 89834527Racemic tert-Butyl-2-benzamido-7a-phenyl-4,4a,5,7-tetrahydropyrrolo[3,4-d][1,3]thiazine-6-carboxylate

Product 1

HCID 89834590tert-Butyl (4aR,7aS)-2-(benzoylamino)-7a-phenyl-4a,5,7,7a-tetrahydropyrrolo[3,4-d][1,3]thiazine-6(4H)-carboxylate

Reagents, catalysts & solvents 1

HCID 21889567Chloroform ethanolSolvent

Procedure

Racemic tert-butyl-2-benzamido-7a-phenyl-4,4a,5,7-tetrahydropyrrolo[3,4-d][1,3]thiazine-6-carboxylate (1.6 g, 3.66 mmol) is dissolved in ethanol/chloroform (30 ml/14 ml) and is separated into its constituent enantiomers by chiral SFC (Supercritical Fluid Chromatography) (Chiralpak AD 8×40.5 cm (20 μm); eluent: 100% ethanol in CO2; flow: 350 mL/min at UV 280 nm; 0.4 g/injection). The first eluting isomer is the title compound (593 mg, 37%). Chiral analysis of this isomer: (Chiralpak AD-H 4.6×150 mm; eluent: 100% ethanol with 0.2% isopropyl amine) in CO2; flow 1 mL/min at UV 225 nm) Rt=3.03 to (>98% ee). ES/MS (m/e): 438 (M+H).

Workup

  1. customis separated into its constituent enantiomers by chiral SFC (Supercritical Fluid Chromatography) (Chiralpak AD 8×40.5 cm (20 μm); eluent: 100% ethanol in CO2; flow: 350 mL/min at UV 280 nm; 0.4 g/injection)

Sources & evidence

ORD record
ord-c7b071e0ae9a4932aae7752f16038134
Source dataset
uspto-grants-2014_11
Patent number
US08889856B2

Reaction notes

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