Acetic Acid → HCID 54503523, compound

HRID 1579432Notes

Reaction equation

HRID 1579432 reaction equation
CS(O[C@@H:6]1[C:23]2[C@:18]([CH3:25])([CH2:19][CH2:20][C:21](=[O:24])[CH:22]=2)[C@@H:17]2[C@H:8]([C@H:9]3[C@@:13]([CH2:15][CH2:16]2)([CH3:14])[C:12](=[O:26])[CH2:11][CH2:10]3)[C@@H:7]1OS(C)(=O)=O)(=O)=O.[N-:32]=[N+:33]=[N-:34].[Na+].C(O)(=O)C>CO>[N:32]([C:6]1[C:23]2[C@:18]([CH3:25])([CH2:19][CH2:20][C:21](=[O:24])[CH:22]=2)[C@@H:17]2[C@H:8]([C@H:9]3[C@@:13]([CH2:15][CH2:16]2)([CH3:14])[C:12](=[O:26])[CH2:11][CH2:10]3)[CH:7]=1)=[N+:33]=[N-:34]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 33557Sodium AzideHCID 86732878HCID 86732878, compound

Product 1

HCID 54503523HCID 54503523, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Conversion of 6α,7α-dihydroxy-4-androstene-3,17-dione to the corresponding 6α,7α-dimethanesulfonate ester by treatment with methanesulfonyl chloride in pyridine in a manner similar to that described in Example 22B followed by treatment of the resulting 6α,7α-dimethanesulfonyloxy-4-androstene-3,17-dione with sodium azide in dimethylformamide in a manner similar to that described in above Example 22C does not yield an identifiable amount of 6-azido-4,6-androstadiene-3,17-dione. Similarly, treatment of 6α,7α-dimethanesulfonyloxy-4-androstene-3,17-dione with sodium azide in aqueous methanol in the presence of acetic acid in a manner similar to that described in Example 6, does not yield an identifiable quantity of 6-azido-4,6-androstadiene-3,17-dione.

Sources & evidence

ORD record
ord-c8809be50e8944e18241f9efef77998a
Source dataset
uspto-grants-1976_01
Patent number
US03931167

Reaction notes

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