Acetic Acid → HCID 69035105, compound

HRID 351369Notes

Reaction equation

HRID 351369 reaction equation
[NH2:1][C@@H:2]1[CH2:7][CH2:6][C@H:5]([N:8]2[CH2:13][CH2:12][C:11]([C:14]3[CH:19]=[CH:18][CH:17]=[C:16]([C:20]([F:23])([F:22])[F:21])[CH:15]=3)=[CH:10][C:9]2=[O:24])[C@H:4]([CH2:25][S:26]([C:29]2[CH:34]=[CH:33][C:32]([S:35][CH3:36])=[CH:31][CH:30]=2)(=[O:28])=[O:27])[CH2:3]1.C(O)(=O)C.[CH3:41][C:42]([CH3:44])=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClC(Cl)C>[CH:42]([NH:1][C@@H:2]1[CH2:7][CH2:6][C@H:5]([N:8]2[CH2:13][CH2:12][C:11]([C:14]3[CH:19]=[CH:18][CH:17]=[C:16]([C:20]([F:23])([F:22])[F:21])[CH:15]=3)=[CH:10][C:9]2=[O:24])[C@H:4]([CH2:25][S:26]([C:29]2[CH:30]=[CH:31][C:32]([S:35][CH3:36])=[CH:33][CH:34]=2)(=[O:28])=[O:27])[CH2:3]1)([CH3:44])[CH3:41]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 180AcetoneHCID 5049666Sodium triacetoxyborohydrideHCID 69035648HCID 69035648, compound

Product 1

HCID 69035105HCID 69035105, compound

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of (±) 1-[(1S*,2R*,4R*)-4-amino-2-(4-methylsulfanyl-benzenesulfonylmethyl)-cyclohexyl]-4-(3-trifluoromethyl-phenyl)-5,6-dihydro-1H-pyridin-2-one (0.36 mmol) in dichloroethane (6 mL) was added acetic acid (0.1 mL, 1.8 mmol), acetone (0.08 mL, 1.1 mmol), and sodium triacetoxyborohydride (0.23 g, 1.1 mmol). The mixture was heated at 80° C. for 1 h, cooled to rt, and quenched with sat. NaHCO3, and extracted twice with EtOAc. The organic extracts were combined, washed with brine, dried (Na2SO4), filtered, and concentrated in vacuo. A portion of the crude residue was purified by reverse-phase HPLC to provide two fractions, one of which contained the title. MS found: (M+H)+=581.

Workup

  1. temperaturecooled to rt
  2. customquenched with sat. NaHCO3
  3. extractionextracted twice with EtOAc
  4. washwashed with brine
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customA portion of the crude residue was purified by reverse-phase HPLC
  9. customto provide two fractions, one of which

Sources & evidence

ORD record
ord-aaa1073b74a84359b5ecc988a2c7d9e5
Source dataset
uspto-grants-2007_02
Patent number
US07183270B2

Reaction notes

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