Dichloroacetic Acid → 3beta-benzoyloxy-21,21-dimethoxy-20-methyl-1alpha-(N-methylcarbamoyl)oxy-7alpha-(methoxycarbonyl)oxypregn-5-ene

HRID 1196371Notes

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.[C:48](=[O:53])([O:51]C)[O:49][CH3:50]>>[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][C@@H:14]([O:53][C:48]([O:49][CH3:50])=[O:51])[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:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

Reactant 3

HCID 6597Dichloroacetic Acid

HCID 12021Dimethyl Carbonate

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

Product 1

HCID 678529553beta-benzoyloxy-21,21-dimethoxy-20-methyl-1alpha-(N-methylcarbamoyl)oxy-7alpha-(methoxycarbonyl)oxypregn-5-ene

Procedure

In 10 ml of dimethyl carbonate was dissolved 350 mg of 3β-benzoyloxy-21,21-dimethoxy-20-methyl-1α-(N-methylcarbamoyl)oxypregn-6-en-5α-ol, followed by addition of 50 mg of dichloroacetic acid, and the mixture was heated in an atmosphere of argon gas for 12 hours. The reaction mixture was then worked up in the same manner as Example 132 to give 90 mg of 3β-benzoyloxy-21,21-dimethoxy-20-methyl-1α-(N-methylcarbamoyl)oxy-7α-(methoxycarbonyl)oxypregn-5-ene showing the following physical properties.

Workup

temperaturethe mixture was heated in an atmosphere of argon gas for 12 hours

Sources & evidence

ORD record: ord-8aaad610fdb34cd9b5a0581ee6584681
Source dataset: uspto-grants-1992_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05112998

Reaction notes

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