HCID 57504918, compound → HCID 66848225, compound

HRID 2060786Notes

Reaction equation

HRID 2060786 reaction equation
[Si]([O:8][CH:9]1[CH2:26][C:12]2([C:27]3[CH:28]=[C:29]([C:33]4[CH:38]=[CH:37][CH:36]=[C:35]([O:39][CH3:40])[CH:34]=4)[CH:30]=[CH:31][CH:32]=3)[N:13]=[C:14]([NH:17][C:18](=[O:25])[C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[S:15][CH2:16][CH:11]2[CH2:10]1)(C(C)(C)C)(C)C.F[Si-2](F)(F)(F)(F)F.[H+].[H+]>C(#N)C.C(OCC)(=O)C>[OH:8][CH:9]1[CH2:26][C:12]2([C:27]3[CH:28]=[C:29]([C:33]4[CH:38]=[CH:37][CH:36]=[C:35]([O:39][CH3:40])[CH:34]=4)[CH:30]=[CH:31][CH:32]=3)[N:13]=[C:14]([NH:17][C:18](=[O:25])[C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=3)[S:15][CH2:16][CH:11]2[CH2:10]1

Participants

4

Reactant 1

HCID 57504918HCID 57504918, compound

Product 1

HCID 66848225HCID 66848225, compound

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of racemic N-((4aRS,6RS,7aSR)-6-(tert-butyldimethylsilyloxy)-7a-(3′-methoxybiphenyl-3-yl)-4,4a,5,6,7,7a-hexahydrocyclopenta[d][1,3]thiazin-2-yl)benzamide (1.47 g, 2.31 mmol) in acetonitrile (6 mL) is added 20-25% aqueous fluorosilicic acid (2.82 g, 4.62 mmol) and the resulting mixture is stirred at room temperature for 3 h. The reaction is diluted with ethyl acetate and quenched with saturated aqueous sodium bicarbonate. The mixture is washed with water and brine. The organic layer is dried over sodium sulfate, filtered, and concentrated under reduced pressure. The crude product is purified by silica gel chromatography eluting with a linear gradient of 10% to 60% ethyl acetate in hexanes over 40 minutes to give the title compound as a racemic mixture (0.709 g, 64%). ES/MS m/e: 459 (M+1).

Workup

  1. customquenched with saturated aqueous sodium bicarbonate
  2. washThe mixture is washed with water and brine
  3. dry with materialThe organic layer is dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe crude product is purified by silica gel chromatography
  7. washeluting with a linear gradient of 10% to 60% ethyl acetate in hexanes over 40 minutes

Sources & evidence

ORD record
ord-11a8877ebbe64bbcb1ac47a486019d05
Source dataset
uspto-grants-2012_10
Patent number
US08278441B2

Reaction notes

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