HCID 66848225, compound → HCID 57504914, compound

HRID 2060787Notes

Reaction equation

HRID 2060787 reaction equation
[OH:1][CH:2]1[CH2:19][C:5]2([C:20]3[CH:21]=[C:22]([C:26]4[CH:31]=[CH:30][CH:29]=[C:28]([O:32][CH3:33])[CH:27]=4)[CH:23]=[CH:24][CH:25]=3)[N:6]=[C:7]([NH:10][C:11](=[O:18])[C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[S:8][CH2:9][CH:4]2[CH2:3]1.CC(O)C.C(=O)=O>>[OH:1][C@H:2]1[CH2:19][C@:5]2([C:20]3[CH:21]=[C:22]([C:26]4[CH:31]=[CH:30][CH:29]=[C:28]([O:32][CH3:33])[CH:27]=4)[CH:23]=[CH:24][CH:25]=3)[N:6]=[C:7]([NH:10][C:11](=[O:18])[C:12]3[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=3)[S:8][CH2:9][C@@H:4]2[CH2:3]1

Participants

3

Reactant 2

HCID 66848225HCID 66848225, compoundHCID 86586944Isopropanol carbon dioxide

Product 1

HCID 57504914HCID 57504914, compoundYield 35.2%

Procedure

Racemic N-((4aRS,6RS,7aSR)-6-hydroxy-7a-(3′-methoxybiphenyl-3-yl)-4,4a,5,6,7,7a-hexahydrocyclopenta[d][1,3]thiazin-2-yl)benzamide (0.689 g, 1.50 mmol) is purified by chiral HPLC: 2.1×25 cm Chiralpak AD-H, 5 micron, 35% IPA/CO2, flow rate: 70 mL/min, UV: 225 nm. The first eluting isomer is isolated to provide the enantiomerically enriched title compound (0.242 g, 35%). ES/MS m/e: 459 (M+1).

Workup

  1. customThe first eluting isomer is isolated

Sources & evidence

ORD record
ord-b350a782cd9e4e68b4da8ef392198721
Source dataset
uspto-grants-2012_10
Patent number
US08278441B2

Reaction notes

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