Trifluoroacetic acid → 17beta-N,N-Diethylcarbamoyl-6-azaandrost-1,4-dien-3-one
Reaction equation
[CH2:1]([N:3]([CH2:33][CH3:34])[C:4]([C@H:6]1[CH2:14][CH2:13][C@H:12]2[C@H:15]3[C@H:25]([CH2:26][CH2:27][C@:7]12[CH2:8]C(O)=O)[C@:23]1([CH3:24])[C:18](=[CH:19][C:20](=[O:28])[CH:21]=[CH:22]1)[N:17](C(C)(C)C)[CH2:16]3)=[O:5])[CH3:2].FC(F)(F)C(O)=O>>[CH2:33]([N:3]([CH2:1][CH3:2])[C:4]([C@H:6]1[CH2:14][CH2:13][C@H:12]2[C@H:15]3[C@H:25]([CH2:26][CH2:27][C@:7]12[CH3:8])[C@:23]1([CH3:24])[C:18](=[CH:19][C:20](=[O:28])[CH:21]=[CH:22]1)[NH:17][CH2:16]3)=[O:5])[CH3:34]Participants
3
Procedure
A sample of 17β-N,N-diethylcarbamoyl-6-t-butylcarboxy-6-azaandrost-1,4-dien-3-one (188 mg, 0.400 mmol), prepared in part B above, is treated with trifluoroacetic acid as described in Example 4 above to give, after trituration with diethyl ether/hexanes 17β-N,N-diethylcarbamoyl-6-azaandrost-1,4-dien-3-one as a pale yellow solid; yield: 98 mg (66%); m.p.>250° C. Anal. Calcd. for C23H34N2O2 ·1/2H2O; C, 72.78; H, 9.29; N, 7.38. Found: C, 72.89; H, 9.20; N, 7.43.
Workup
- customto give
Sources & evidence
- ORD record
- ord-d5cbaba702924664a28d244977ae7b47
- Source dataset
- uspto-grants-1996_08
- Patent number
- US05543406
Reaction notes
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