Hexane → HCID 57504915, compound

HRID 2060788Notes

Reaction equation

HRID 2060788 reaction equation
[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:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[S:8][CH2:9][C@@H:4]2[CH2:3]1.F[B-](F)(F)F.[H+].[CH3:40][Si](C=[N+]=[N-])(C)C.CCCCCC.C(=O)(O)[O-].[Na+]>ClCCl.O>[CH3:40][O: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

8

Reactant 5

HCID 8058HexaneHCID 28118Tetrafluoroboric acidHCID 167693TrimethylsilyldiazomethaneHCID 516892Sodium BicarbonateHCID 57504914HCID 57504914, compound

Product 1

HCID 57504915HCID 57504915, compoundYield 48%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a 0° C. mixture of N-((4aR,6R,7aS)-6-hydroxy-7a-(3′-methoxybiphenyl-3-yl)-4,4a,5,6,7,7a-hexahydrocyclopenta[d][1,3]thiazin-2-yl)benzamide (0.086 g, 0.169 mmol) and 48% aqueous fluoroboric acid (0.031 g, 0.169 mmol) in dichloromethane (0.6 mL) is added 2 M trimethylsilyldiazomethane in hexane (0.101 mL, 0.202 mmol). The mixture is stirred at 0° C. for 30 minutes and is poured into saturated aqueous solution of sodium bicarbonate. The mixture is diluted with water and is extracted with dichloromethane. The organic layer is washed sequentially with water and brine and is dried over sodium sulfate. The solvent is removed under reduced pressure and the crude product is purified by silica gel chromatography eluting with a linear gradient of 10% to 60% ethyl acetate in hexanes over 20 minutes to give the title compound (0.038 g, 48%). ES/MS m/e: 473 (M+1).

Workup

  1. extractionis extracted with dichloromethane
  2. washThe organic layer is washed sequentially with water and brine
  3. dry with materialis dried over sodium sulfate
  4. customThe solvent is removed under reduced pressure
  5. customthe crude product is purified by silica gel chromatography
  6. washeluting with a linear gradient of 10% to 60% ethyl acetate in hexanes over 20 minutes

Sources & evidence

ORD record
ord-1edb6624ab74459fa9d4738a37b183de
Source dataset
uspto-grants-2012_10
Patent number
US08278441B2

Reaction notes

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