Pyridine → HCID 86744602, compound

HRID 981467Notes

Reaction equation

HRID 981467 reaction equation
[OH:1][CH:2]([CH:6]([S:21][CH2:22][C:23](=[O:30])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[C:13]1[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=1)[C:3]([NH2:5])=[O:4].N1C=CC=CC=1.[C:37](Cl)(=[O:39])[CH3:38]>C(Cl)Cl>[C:37]([O:1][CH:2]([CH:6]([S:21][CH2:22][C:23](=[O:30])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[C:13]1[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=1)[C:3]([NH2:5])=[O:4])(=[O:39])[CH3:38]

Participants

5

Reactant 3

HCID 1049PyridineHCID 6367Acetyl chlorideHCID 86744603alpha-Hydroxy-4-methoxyphenyl-beta-[(2-oxo-2-phenylethyl) thio]benzenepropanamide

Product 1

HCID 86744602HCID 86744602, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a mixture of 4.0 g (0.0116 mol) of rac.-(R, R*)-α-hydroxy-4-methoxyphenyl-β-[(2-oxo-2-phenylethyl) thio]benzenepropanamide, 130 mL of methylene chloride and 5 mL of pyridine cooled in an ice-bath was added dropwise a solution of 1.25 g (0.0126 mol) of acetyl chloride in 25 mL of methylene chloride. The mixture was stirred at this temperature for one hour and at room temperature for 17 hours. After dilution with water the aqueous suspension was extracted with methylene chloride. The methylene chloride solution was dried (MgSO4) and removal of the solvent gave a residue which was washed with hexane. The crude product was crystallized from ethyl acetate to give 4.1 g (93%) of rac.-(R,*R*)-α-(acetyloxy)-4-methoxyphenyl-β-[(2-oxo-2-phenylethyl)thio]benzeneprop anamide, mp 154°-155°.

Workup

  1. temperaturecooled in an ice-bath
  2. extractionAfter dilution with water the aqueous suspension was extracted with methylene chloride
  3. dry with materialThe methylene chloride solution was dried
  4. custom(MgSO4) and removal of the solvent
  5. customgave a residue which
  6. washwas washed with hexane
  7. customThe crude product was crystallized from ethyl acetate

Sources & evidence

ORD record
ord-9c8b1922af5d44e8b7ff4b32a0961414
Source dataset
uspto-grants-1991_02
Patent number
US04992432

Reaction notes

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