Methanesulfonyl chloride → HCID 54503523, compound

HRID 1579431Notes

Reaction equation

HRID 1579431 reaction equation
O[C@@H:2]1[C:19]2[C@:14]([CH3:21])([CH2:15][CH2:16][C:17](=[O:20])[CH:18]=2)[C@@H:13]2[C@H:4]([C@H:5]3[C@@:9]([CH2:11][CH2:12]2)([CH3:10])[C:8](=[O:22])[CH2:7][CH2:6]3)[C@@H:3]1O.CS(Cl)(=O)=O.CS(O[C@@H]1C2[C@](C)(CCC(=O)C=2)[C@@H]2[C@H]([C@H]3[C@@](CC2)(C)C(=O)CC3)[C@@H]1OS(C)(=O)=O)(=O)=O.[N-:60]=[N+:61]=[N-:62].[Na+]>N1C=CC=CC=1.CN(C)C=O>[N:60]([C:2]1[C:19]2[C@:14]([CH3:21])([CH2:15][CH2:16][C:17](=[O:20])[CH:18]=2)[C@@H:13]2[C@H:4]([C@H:5]3[C@@:9]([CH2:11][CH2:12]2)([CH3:10])[C:8](=[O:22])[CH2:7][CH2:6]3)[CH:3]=1)=[N+:61]=[N-:62]

Participants

7

Reactant 4

HCID 31297Methanesulfonyl chlorideHCID 33557Sodium AzideHCID 68131678HCID 68131678, compoundHCID 86732878HCID 86732878, compound

Product 1

HCID 54503523HCID 54503523, compound

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6228DimethylformamideSolvent

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-f28b1ce9c28e40e09007514742cc68a3
Source dataset
uspto-grants-1976_01
Patent number
US03931167

Reaction notes

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