1alpha,3beta-Bis(methoxycarbonyloxy)pregna-5,7-diene-20-carboxylic acid → Methyl 1alpha,3beta-di-acetoxypregna-5,7-diene-20-carboxylate

HRID 1587623Notes

Reaction equation

HRID 1587623 reaction equation
[C:1]([O:4][C@@H:5]1[C@@:26]2([CH3:27])[C:9](=[CH:10][CH:11]=[C:12]3[C@@H:25]2[CH2:24][CH2:23][C@@:22]2([CH3:28])[C@H:13]3[CH2:14][CH2:15][C@@H:16]2[CH:17]([C:19]([OH:21])=[O:20])[CH3:18])[CH2:8][C@@H:7]([O:29][C:30](=[O:32])[CH3:31])[CH2:6]1)(=[O:3])[CH3:2].[CH3:33]OC(O[C@@H]1[C@@]2(C)C(=CC=C3[C@@H]2CC[C@@]2(C)[C@H]3CC[C@@H]2C(C(O)=O)C)C[C@@H](OC(OC)=O)C1)=O>>[C:1]([O:4][C@@H:5]1[C@@:26]2([CH3:27])[C:9](=[CH:10][CH:11]=[C:12]3[C@@H:25]2[CH2:24][CH2:23][C@@:22]2([CH3:28])[C@H:13]3[CH2:14][CH2:15][C@@H:16]2[CH:17]([C:19]([O:21][CH3:33])=[O:20])[CH3:18])[CH2:8][C@@H:7]([O:29][C:30](=[O:32])[CH3:31])[CH2:6]1)(=[O:3])[CH3:2]

Participants

3

Reactant 2

HCID 537642171alpha,3beta-Bis(methoxycarbonyloxy)pregna-5,7-diene-20-carboxylic acidHCID 541079121alpha,3beta-Diacetoxypregna-5,7-diene-20-carboxylic acid

Product 1

HCID 54298465Methyl 1alpha,3beta-di-acetoxypregna-5,7-diene-20-carboxylateYield 100.3%

Procedure

The procedure of Example 7 was repeated except that 89 mg of 1α,3β-diacetoxypregna-5,7-diene-20-carboxylic acid obtained in Example 22 was used in lieu of 85 mg of 1α,3β-bis(methoxycarbonyloxy)pregna-5,7-diene-20-carboxylic acid to give 82 mg of methyl 1α,3β-di-acetoxypregna-5,7-diene-20-carboxylate.

Sources & evidence

ORD record
ord-938900ca4afa41b589837cbf134d3d99
Source dataset
uspto-grants-1993_06
Patent number
US05218109

Reaction notes

Loading…