Chloroacetic Acid → 20-(1,3-Dioxolan-2yl)-3beta-acetoxy-1alpha-benzoyloxypregna-5,7-diene

HRID 1708797Notes

Reaction equation

HRID 1708797 reaction equation
[O:1]1[CH2:5][CH2:4][O:3][CH:2]1[CH:6]([C@@H:8]1[C@:25]2([CH3:26])[C@H:11]([C@H:12]3[C@H:22]([CH2:23][CH2:24]2)[C@:20]2([CH3:21])[C@:15](O)([CH2:16][C@@H:17]([O:36][C:37](=[O:39])[CH3:38])[CH2:18][C@@H:19]2[O:27][C:28](=[O:35])[C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[CH:14]=[CH:13]3)[CH2:10][CH2:9]1)[CH3:7].ClCC(O)=O>C(=O)(OCC)OCC>[O:1]1[CH2:5][CH2:4][O:3][CH:2]1[CH:6]([C@@H:8]1[C@:25]2([CH3:26])[C@H:11]([C:12]3[C@H:22]([CH2:23][CH2:24]2)[C@:20]2([CH3:21])[C:15]([CH2:16][C@@H:17]([O:36][C:37](=[O:39])[CH3:38])[CH2:18][C@@H:19]2[O:27][C:28](=[O:35])[C:29]2[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=2)=[CH:14][CH:13]=3)[CH2:10][CH2:9]1)[CH3:7]

Participants

4

Reactant 2

HCID 300Chloroacetic AcidHCID 6785296120-(1,3-Dioxolan-2-yl)-3beta-acetoxy-1alpha-benzoyloxypregn-6-en-5alpha-ol

Product 1

HCID 6785298420-(1,3-Dioxolan-2yl)-3beta-acetoxy-1alpha-benzoyloxypregna-5,7-dieneYield 35.4%

Reagents, catalysts & solvents 1

HCID 7766Diethyl CarbonateSolvent

Conditions

Temperature
100 °C

Procedure

In 10 ml of diethyl carbonate was dissolved 350 mg of 20-(1,3-dioxolan-2-yl)-3β-acetoxy-1α-benzoyloxypregn-6-en-5α-ol, followed by addition of 0.1 ml of monochloroacetic acid. The mixture was stirred under heating at 100° C. in an atmosphere of argon gas for 10 hours. The reaction mixture was then worked up in the same manner as Example 124 to give 120 mg of 20-(1,3-dioxolan-2-yl)-3β-acetoxy-1α-benzoyloxypregna-5,7-diene showing the following physical properties.

Sources & evidence

ORD record
ord-a01d0255f27e4e7ab1569116d4e07aee
Source dataset
uspto-grants-1994_10
Patent number
US05359055

Reaction notes

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