Water → 3beta-benzoyloxy-1alpha-(N-methylcarbamoyl)oxypregna-5,7-diene-20-carbaldehyde

HRID 1196383Notes

Reaction equation

HRID 1196383 reaction equation
[C:1]([O:9][C@H:10]1[CH2:33][C@H:32]([O:34][C:35](=[O:38])[NH:36][CH3:37])[C@@:31]2([CH3:39])[C:12](=[CH:13][CH:14]=[C:15]3[C@@H:30]2[CH2:29][CH2:28][C@@:27]2([CH3:40])[C@H:16]3[CH2:17][CH2:18][C@@H:19]2[CH:20]([CH3:26])[CH:21](OC)[O:22]C)[CH2:11]1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O>CO.S([O-])([O-])(=O)=O.[Cu+2]>[C:1]([O:9][C@H:10]1[CH2:33][C@H:32]([O:34][C:35](=[O:38])[NH:36][CH3:37])[C@@:31]2([CH3:39])[C:12](=[CH:13][CH:14]=[C:15]3[C@@H:30]2[CH2:29][CH2:28][C@@:27]2([CH3:40])[C@H:16]3[CH2:17][CH2:18][C@@H:19]2[CH:20]([CH:21]=[O:22])[CH3:26])[CH2:11]1)(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 962WaterHCID 678529803beta-benzoyloxy-21,21-dimethoxy-20-methyl-1alpha-(N-methylcarbamoyl)oxypregna-5,7-diene

Product 1

HCID 867458323beta-benzoyloxy-1alpha-(N-methylcarbamoyl)oxypregna-5,7-diene-20-carbaldehydeYield 65.5%

Reagents, catalysts & solvents 2

HCID 24462Copper SulfateCatalystHCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

In 5 ml of methanol was dissolved 100 mg of 3β-benzoyloxy-21,21-dimethoxy-20-methyl-1α-(N-methylcarbamoyl)oxypregna-5,7-diene, followed by addition of 5 ml of water and 100 mg of copper sulfate. The mixture was stirred in an atmosphere of argon gas at a temperature of 60° C. for 7 hours. The reaction mixture was then worked up in the same manner as Example 156 to give 60 mg of 3β-benzoyloxy-1α-(N-methylcarbamoyl)oxypregna-5,7-diene-20-carbaldehyde showing the following physical properties.

Sources & evidence

ORD record
ord-889f90d0cb87415b8be7db433b8a6389
Source dataset
uspto-grants-1992_05
Patent number
US05112998

Reaction notes

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