Diethylamine → 17beta-N,N-diethylcarbamoyl-6-t-butylcarboxy-6-azaandrost-1,4-dien-3-one

HRID 1077597Notes

Reaction equation

[C:1]([C@H:5]1[CH2:13][CH2:12][C@H:11]2[C@H:14]3[C@H:24]([CH2:25][CH2:26][C@:6]12[CH2:7][C:8]([OH:10])=[O:9])[C@:22]1([CH3:23])[C:17](=[CH:18][C:19](=[O:27])[CH:20]=[CH:21]1)[N:16]([C:28]([CH3:31])([CH3:30])[CH3:29])[CH2:15]3)(OC)=[O:2].[CH2:32]([NH:34][CH2:35][CH3:36])[CH3:33]>>[CH2:32]([N:34]([CH2:35][CH3:36])[C:1]([C@H:5]1[CH2:13][CH2:12][C@H:11]2[C@H:14]3[C@H:24]([CH2:25][CH2:26][C@:6]12[CH2:7][C:8]([OH:10])=[O:9])[C@:22]1([CH3:23])[C:17](=[CH:18][C:19](=[O:27])[CH:20]=[CH:21]1)[N:16]([C:28]([CH3:31])([CH3:30])[CH3:29])[CH2:15]3)=[O:2])[CH3:33]

Participants

Reactant 2

HCID 8021Diethylamine

HCID 8674971017beta-Carbomethoxy-6-t-butylcarboxy-6-azaandrost-1,4-dien-3-one

Product 1

HCID 8674971117beta-N,N-diethylcarbamoyl-6-t-butylcarboxy-6-azaandrost-1,4-dien-3-oneYield 50%

Procedure

The crude 17β-carbomethoxy-6-t-butylcarboxy-6-azaandrost-1,4-dien-3-one (1.50 g, 3.50 mmol), prepared in part A, is hydrolyzed as in Example 3, part F and then coupled with diethylamine as described in Example 1, part A to give after chromatography (50% ethyl acetate/hexanes) 17β-N,N-diethylcarbamoyl-6-t-butylcarboxy-6-azaandrost-1,4-dien-3-one as a white foam; yield: 1.07 g (65%). Anal. Calcd. for C28H42N2O4 ; C, 71.45; H, 9.00; N, 5.95. Found C, 71.38; H, 9.07; N, 5.90.

Sources & evidence

ORD record: ord-c528c6d50a97463a961935268cf1a7dd
Source dataset: uspto-grants-1996_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05543406

Reaction notes

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