HCID 89832300, compound → HCID 89832307, compound

HRID 338123Notes

Reaction equation

HRID 338123 reaction equation
[CH2:1]([N:4]1[CH2:12][CH:11]2[C:6]([C:22]3[S:23][C:24]([F:27])=[CH:25][CH:26]=3)([N:7]=[C:8]([NH:13][C:14](=[O:21])[C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[S:9][CH2:10]2)[CH2:5]1)[CH:2]=[CH2:3]>CO.C(Cl)(Cl)Cl>[F:27][C:24]1[S:23][C:22]([C@:6]23[CH2:5][N:4]([CH2:1][CH:2]=[CH2:3])[CH2:12][C@H:11]2[CH2:10][S:9][C:8]([NH:13][C:14](=[O:21])[C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)=[N:7]3)=[CH:26][CH:25]=1

Participants

3

Reactant 1

HCID 89832300HCID 89832300, compound

Product 1

HCID 89832307HCID 89832307, compound

Reagents, catalysts & solvents 1

HCID 21584188Chloroform methanolSolvent

Procedure

Racemic N-[6-allyl-7a-(5-fluoro-2-thienyl)-4,4a,5,7-tetrahydropyrrolo[3,4-d][1,3]thiazin-2-yl]benzamide (4.71 g, 11.73 mmol) is dissolved in 1:1 MeOH/CHCl3 (20 mg/mL) and separated into its constituent enantiomers by chiral HPLC (Column: Chiralcel OD 8×32 cm (20 μM); mobile phase: 60:40 IPA/heptane; flow rate 385 mL/min at UV 290 nm; 0.320 g/injection). Analysis of the second eluting isomer (Column: Chiralcel OD-H 4.6×150 mm; mobile phase: 60:40 IPA/heptane; flow rate 0.6 mL/min at UV 290 nm) gave the title compound, Rt=8.2 minutes (2.01 g, 43%, 96.1% ee). ES/MS (m/e): 402.0 (M+H).

Workup

  1. customseparated into its constituent enantiomers by chiral HPLC (Column: Chiralcel OD 8×32 cm (20 μM); mobile phase: 60:40 IPA/heptane; flow rate 385 mL/min at UV 290 nm; 0.320 g/injection)

Sources & evidence

ORD record
ord-15689fbc00c4427497639d71f796ed2c
Source dataset
uspto-grants-2014_11
Patent number
US08889856B2

Reaction notes

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