21,21-Dimethoxy-20-methylpregn-6-ene-1alpha,3beta,5a-triol → 20-(1,3-Dioxolan-2-yl)-3beta-acetoxy-1alpha-benzoyloxypregn-6-en-5alpha-ol

HRID 1708796Notes

Reaction equation

HRID 1708796 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]([OH:32])([CH2:16][C@@H:17]([O:28][C:29](=[O:31])[CH3:30])[CH2:18][C@@H:19]2[OH:27])[CH:14]=[CH:13]3)[CH2:10][CH2:9]1)[CH3:7].COC(OC)C(C)[C@@H]1[C@]2(C)[C@H]([C@H:41]3[C@H:51](CC2)[C@:49]2(C)[C@:44](O)(C[C@@H](O)C[C@@H:48]2[OH:56])[CH:43]=[CH:42]3)CC1>>[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]([OH:32])([CH2:16][C@@H:17]([O:28][C:29](=[O:31])[CH3:30])[CH2:18][C@@H:19]2[O:27][C:48](=[O:56])[C:49]2[CH:51]=[CH:41][CH:42]=[CH:43][CH:44]=2)[CH:14]=[CH:13]3)[CH2:10][CH2:9]1)[CH3:7]

Participants

3

Reactant 2

HCID 5708541221,21-Dimethoxy-20-methylpregn-6-ene-1alpha,3beta,5a-triolHCID 6785296520-(1,3-Dioxolan-2-yl)-3beta-acetoxypregn-6-ene-1alpha,5alpha-diol

Product 1

HCID 6785296120-(1,3-Dioxolan-2-yl)-3beta-acetoxy-1alpha-benzoyloxypregn-6-en-5alpha-olYield 92.8%

Procedure

The reaction and workup procedures of Example 105 were repeated except that 350 mg of 20-(1,3-dioxolan-2-yl)-3β-acetoxypregn-6-ene-1α,5α-diol was used in lieu of 400 mg of 21,21-dimethoxy-20-methylpregn-6-ene-1α,3β,5α-triol to give 400 mg of 20-(1,3-dioxolan-2-yl)-3β-acetoxy-1α-benzoyloxypregn-6-en-5α-ol showing the following physical properties.

Workup

  1. customThe reaction and workup procedures of Example 105

Sources & evidence

ORD record
ord-99bebc4f970d4b75985bf65e3295ae74
Source dataset
uspto-grants-1994_10
Patent number
US05359055

Reaction notes

Loading…