(+)-Methyl 5-(3-(hydroxymethyl)phenyl)-8-dimethylcarbamyl-4,6-dithiaoctanoate → (+)-Methyl 5-(3-formylphenyl)-8-dimethylcarbamyl-4,6-dithiaoctanoate

HRID 22604

Reaction equation

HRID 22604 reaction equation
[OH:1][CH2:2][C:3]1[CH:4]=[C:5]([CH:9]([S:17][CH2:18][CH2:19][C:20](=[O:24])[N:21]([CH3:23])[CH3:22])[S:10][CH2:11][CH2:12][C:13]([O:15][CH3:16])=[O:14])[CH:6]=[CH:7][CH:8]=1>C(OCC)(=O)C.[O-2].[Mn+2]>[CH:2]([C:3]1[CH:4]=[C:5]([CH:9]([S:17][CH2:18][CH2:19][C:20](=[O:24])[N:21]([CH3:23])[CH3:22])[S:10][CH2:11][CH2:12][C:13]([O:15][CH3:16])=[O:14])[CH:6]=[CH:7][CH:8]=1)=[O:1]

Participants

4

Reactant 1

HCID 19930508(+)-Methyl 5-(3-(hydroxymethyl)phenyl)-8-dimethylcarbamyl-4,6-dithiaoctanoate

Product 1

HCID 19930537(+)-Methyl 5-(3-formylphenyl)-8-dimethylcarbamyl-4,6-dithiaoctanoate

Reagents, catalysts & solvents 2

HCID 160959Manganese oxideCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (-)-methyl 5-(3-(hydroxymethyl)phenyl)-8-dimethylcarbamyl-4,6-dithiaoctanoate (step 6) (679 mg) in ethyl acetate (30 mL) was added activated manganese oxide (1.3 g). The suspension was stirred overnight at room temperature. The suspension was filtered on a pad of silica gel and washed with EtOAc. The solvent was evaporated, affording the title compound.

Workup

  1. filtrationThe suspension was filtered on a pad of silica gel
  2. washwashed with EtOAc
  3. customThe solvent was evaporated

Sources & evidence

ORD record
ord-2c76c6390c874a68b5f67e1f897e1a62
Source dataset
uspto-grants-1995_06
Patent number
US05428171

Linked notes

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