Benzoic Acid → 2-Benzoyl-17beta-methoxy-5alpha-androstan-3-one

HRID 848787Notes

Reaction equation

HRID 848787 reaction equation
[CH3:1][O:2][C@H:3]1[CH2:8][CH2:7][C@H:6]2[C@H:9]3[C@H:19]([CH2:20][CH2:21][C@:4]12[CH3:5])[C@:17]1([CH3:18])[C@H:12]([CH2:13][C:14](=[O:22])[CH2:15][CH2:16]1)[CH2:11][CH2:10]3.[C:23](O)(=[O:30])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.C(OC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1.C(OC(=O)C)(=O)C>>[C:23]([CH:15]1[CH2:16][C@@:17]2([CH3:18])[C@@H:12]([CH2:11][CH2:10][C@@H:9]3[C@@H:19]2[CH2:20][CH2:21][C@@:4]2([CH3:5])[C@H:6]3[CH2:7][CH2:8][C@@H:3]2[O:2][CH3:1])[CH2:13][C:14]1=[O:22])(=[O:30])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

5

Reactant 4

HCID 243Benzoic AcidHCID 7167Benzoic anhydrideHCID 7918Acetic AnhydrideHCID 1104493517beta-Methoxy-5alpha-androstan-3-one

Product 1

HCID 705622692-Benzoyl-17beta-methoxy-5alpha-androstan-3-one

Procedure

Following the general procedure of U.S. Pat. No. 3,135,743, Example 12, but starting with 17β-methoxy-5α-androstan-3-one and using benzoic acid and benzoic acid anhydride in place of acetic acid and acetic anhydride, 2-benzoyl-17β-methoxy-5α-androstan-3-one is obtained.

Sources & evidence

ORD record
ord-dc46de435ac64f1f91dde8b8b3f9dc13
Source dataset
uspto-grants-1981_10
Patent number
US04297350

Reaction notes

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