1alpha,3beta-Bis(methoxycarbonyloxy)pregna-5,7-diene-20-carbaldehyde → 1alpha,3beta-Diacetoxypregna-5,7-diene-20-carboxylic acid

HRID 1587620Notes

Reaction equation

HRID 1587620 reaction equation
[C:1]([O:4][C@@H:5]1[C@@:25]2([CH3:26])[C:9](=[CH:10][CH:11]=[C:12]3[C@@H:24]2[CH2:23][CH2:22][C@@:21]2([CH3:27])[C@H:13]3[CH2:14][CH2:15][C@@H:16]2[CH:17]([CH:19]=[O:20])[CH3:18])[CH2:8][C@@H:7]([O:28][C:29](=[O:31])[CH3:30])[CH2:6]1)(=[O:3])[CH3:2].C[O:33]C(O[C@@H]1[C@@]2(C)C(=CC=C3[C@@H]2CC[C@@]2(C)[C@H]3CC[C@@H]2C(C=O)C)C[C@@H](OC(OC)=O)C1)=O>>[C:1]([O:4][C@@H:5]1[C@@:25]2([CH3:26])[C:9](=[CH:10][CH:11]=[C:12]3[C@@H:24]2[CH2:23][CH2:22][C@@:21]2([CH3:27])[C@H:13]3[CH2:14][CH2:15][C@@H:16]2[CH:17]([C:19]([OH:33])=[O:20])[CH3:18])[CH2:8][C@@H:7]([O:28][C:29](=[O:31])[CH3:30])[CH2:6]1)(=[O:3])[CH3:2]

Participants

3

Reactant 2

HCID 543675231alpha,3beta-Bis(methoxycarbonyloxy)pregna-5,7-diene-20-carbaldehydeHCID 543796531alpha,3beta-Diacetoxypregna-5,7-diene-20-carbaldehyde

Product 1

HCID 541079121alpha,3beta-Diacetoxypregna-5,7-diene-20-carboxylic acidYield 81.7%

Procedure

The procedure of Example 6 was repeated except that 105 mg of 1α,3β-diacetoxypregna-5,7-diene-20-carbaldehyde was used in lieu of 120 mg of 1α,3β-bis(methoxycarbonyloxy)pregna-5,7-diene-20-carbaldehyde to give 89 mg of 1α,3β-diacetoxypregna-5,7-diene-20-carboxylic acid.

Sources & evidence

ORD record
ord-82693b24efef4bab933fe73e7212a123
Source dataset
uspto-grants-1993_06
Patent number
US05218109

Reaction notes

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