Methanol → HCID 57504898, compound

HRID 2060766Notes

Reaction equation

HRID 2060766 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:8]23[CH2:17][CH2:16][O:15][CH2:14][CH:13]2[CH2:12][S:11][C:10]([NH:18][C:19](=[O:25])[O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[N:9]3)[CH:5]=[CH:6][CH:7]=1.CO>C(#N)C>[Br:1][C:2]1[CH:3]=[C:4]([C@:8]23[CH2:17][CH2:16][O:15][CH2:14][CH:13]2[CH2:12][S:11][C:10]([NH:18][C:19](=[O:25])[O:20][C:21]([CH3:23])([CH3:22])[CH3:24])=[N:9]3)[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 887MethanolHCID 66860802HCID 66860802, compound

Product 1

HCID 57504898HCID 57504898, compoundYield 47%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Racemic tert-butyl (4aSR,8aSR)-8a-(3-bromophenyl)-4,4a,5,7,8,8a-hexahydropyrano[4,3-d][1,3]thiazin-2-ylcarbamate (2.80 g, 6.55 mmol) is purified by chiral HPLC: Column: Chiralcel OJ 8×35 cm; eluent: 75:25 (methanol:acetonitrile); flow: 400 mL/min at UV 260 nm. The second eluting isomer is isolated to provide the enantiomerically enriched title compound (1.31 g, 47%). ES/MS m/e (79Br/81Br) 427, 429 (M+1).

Workup

  1. customThe second eluting isomer is isolated

Sources & evidence

ORD record
ord-6a19a950267b4cb3bb1af60e31a31d74
Source dataset
uspto-grants-2012_10
Patent number
US08278441B2

Reaction notes

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