Dichloroacetic Acid → 3beta-benzoyloxy-21,21-dimethoxy-20-methyl-1alpha-(N-methylcarbamoyl)oxypregna-5,7-diene

HRID 1708798Notes

Reaction equation

HRID 1708798 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](O)([CH:13]=[CH:14][C@@H: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]([O:24][CH3:25])[O:22][CH3:23])[CH2:11]1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.ClC(Cl)C(O)=O>O1CCCC1>[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]([O:24][CH3:25])[O:22][CH3:23])[CH2:11]1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 6597Dichloroacetic AcidHCID 678529103beta-benzoyloxy-21,21-dimethoxy-20-methyl-1alpha-(N-methylcarbamoyl)oxypregn-6-en-5alpha-ol

Product 1

HCID 678529803beta-benzoyloxy-21,21-dimethoxy-20-methyl-1alpha-(N-methylcarbamoyl)oxypregna-5,7-dieneYield 35.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In 10 ml of tetrahydrofuran was dissolved 350 mg of 3β-benzoyloxy-21,21-dimethoxy-20-methyl-1α-(N-methylcarbamoyl)oxypregna-6-en-5α-ol, followed by addition of 50 mg of dichloroacetic acid. The mixture was refluxed in an atmosphere of argon gas for 12 hours. The reaction mixture was then worked up in the same manner as Example 124 to give 120 mg of 3β-benzoyloxy-21,21-dimethoxy-20-methyl-1α-(N-methylcarbamoyl)oxypregna-5,7 -diene showing the following physical properties.

Workup

  1. temperatureThe mixture was refluxed in an atmosphere of argon gas for 12 hours

Sources & evidence

ORD record
ord-c68c3484d7384ec9b5449fb612abf706
Source dataset
uspto-grants-1994_10
Patent number
US05359055

Reaction notes

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