HCID 136333932, compound → HCID 136333930, compound

HRID 1409038Notes

Reaction equation

HRID 1409038 reaction equation
[Br:1][C:2]1[S:10][C:9]2[C:8](=[O:11])[NH:7][C:6]([CH:12]3[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][N:13]3[C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])=[N:5][C:4]=2[CH:3]=1>CCCCCC.C(O)C>[Br:1][C:2]1[S:10][C:9]2[C:8](=[O:11])[NH:7][C:6]([C@H:12]3[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][N:13]3[C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])=[N:5][C:4]=2[CH:3]=1.[Br:1][C:2]1[S:10][C:9]2[C:8](=[O:11])[NH:7][C:6]([C@@H:12]3[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][N:13]3[C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])=[N:5][C:4]=2[CH:3]=1

Participants

4

Reactant 1

HCID 136333932HCID 136333932, compound

Product 2

HCID 136333930HCID 136333930, compoundHCID 136333931HCID 136333931, compound

Reagents, catalysts & solvents 1

HCID 21879635Ethanol hexaneSolvent

Procedure

tert-Butyl 2-(6-bromo-4-oxo-3,4-dihydrothieno[3,2-d]pyrimidin-2-yl)azepane-1-carboxylate (772 mg) produced in Example 79, step A, was fractionated by high performance liquid chromatography (column: CHIRALPAK AD (50 mm i.d.×500 mm L, manufactured by DAICEL CHEMICAL INDUSTRIES, LTD.), mobile phase: hexane/ethanol (500/500), flow rate: 60 mL/min, column temperature: 30° C.). tert-Butyl (2R)-2-(6-bromo-4-oxo-3,4-dihydrothieno[3,2-d]pyrimidin-2-yl)azepane-1-carboxylate (325 mg, >99.9% ee, retention time 11.2 min) and tert-butyl (2S)-2-(6-bromo-4-oxo-3,4-dihydrothieno[3,2-d]pyrimidin-2-yl)azepane-1-carboxylate (326 mg, >99.9% ee, retention time 13.7 min) were obtained under the above-mentioned high performance liquid chromatography conditions. The analysis was performed by high performance liquid chromatography (column: CHIRALPAK AD-H (4.6 mm i.d.×250 mm L, manufactured by DAICEL CHEMICAL INDUSTRIES, LTD.), mobile phase: hexane/ethanol (500/500), flow rate: 0.5 mL/min, column temperature: 30° C., detection 220 nm). The absolute steric configuration after optical resolution was determined by an X-ray crystal structural analysis of the fraction at retention time 13.7 min.

Sources & evidence

ORD record
ord-6901019cd6a346709aa8e736356a8303
Source dataset
uspto-grants-2014_12
Patent number
US08921354B2

Reaction notes

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