Methanol → HCID 57504923, compound

HRID 2060797Notes

Reaction equation

HRID 2060797 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:9]23[CH2:17][CH:16]([OH:18])[CH2:15][CH:14]2[CH2:13][S:12][C:11]([NH:19][C:20](=[O:27])[C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[N:10]3)[CH:5]=[CH:6][C:7]=1[F:8].CO>C(#N)C>[Br:1][C:2]1[CH:3]=[C:4]([C@:9]23[CH2:17][C@H:16]([OH:18])[CH2:15][C@H:14]2[CH2:13][S:12][C:11]([NH:19][C:20](=[O:27])[C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)=[N:10]3)[CH:5]=[CH:6][C:7]=1[F:8]

Participants

4

Reactant 2

HCID 887MethanolHCID 66847985HCID 66847985, compound

Product 1

HCID 57504923HCID 57504923, compoundYield 35%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Racemic N-((4aRS,6RS,7aSR)-7a-(3-bromo-4-fluorophenyl)-6-hydroxy-4,4a,5,6,7,7a-hexahydrocyclopenta[d][1,3]thiazin-2-yl)benzamide (0.492 g, 1.09 mmol) is purified by chiral HPLC: Column: Chiralcel OJ-H 3×25 cm; eluent: 75:25 (methanol:acetonitrile); flow: 40 mL/min at UV 225 nm. The second eluting isomer is isolated to provide the enantiomerically enriched title compound (0.171 g, 35%). ES/MS m/e (79Br/81Br) 449, 451 (M+1).

Workup

  1. customThe second eluting isomer is isolated

Sources & evidence

ORD record
ord-2e44e9b438ff48828d85ab84e51db421
Source dataset
uspto-grants-2012_10
Patent number
US08278441B2

Reaction notes

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