Butyryl chloride → HCID 70447822, compound

HRID 543008Notes

Reaction equation

HRID 543008 reaction equation
[H-].[Na+].[CH2:3]([N:7]([CH2:40]C)[C:8](=[O:39])[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][C@@H:19]1[CH2:36][C:35]2[CH:34]=C(O)C=[CH:31][C:30]=2[C@@H:29]2[C@@H:20]1[C@H:21]1[C@@:25]([CH2:27][CH2:28]2)([CH3:26])[C@@H:24]([OH:38])[CH2:23][CH2:22]1)[CH2:4][CH2:5][CH3:6].[C:42](Cl)(=O)[CH2:43]CC.[C:48]([O:51][CH2:52][CH3:53])(=[O:50])[CH3:49]>O1CCCC1>[CH2:3]([N:7]([CH3:40])[C:8](=[O:39])[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][C@@H:19]1[CH2:36][C:35]2[CH:34]=[C:52]([O:51][C:48](=[O:50])[CH2:49][CH2:42][CH3:43])[CH:53]=[CH:31][C:30]=2[C@@H:29]2[C@@H:20]1[C@H:21]1[C@@:25]([CH2:27][CH2:28]2)([CH3:26])[C@@H:24]([OH:38])[CH2:23][CH2:22]1)[CH2:4][CH2:5][CH3:6]

Participants

6

Reactant 4

HCID 8855Butyryl chlorideHCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 70446874HCID 70446874, compound

Product 1

HCID 70447822HCID 70447822, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Sodium hydride (0.005 g. of a 50% dispersion in mineral oil) was added to a stirred solution of N-n-butyl-11-(3,17β-dihydroxyoestra-1,3,5(10)-trien-7α-yl)-N-ethylundecanamide (Example 2; 0.052 g.) in tetrahydrofuran (2 ml.) and the mixture was stirred at laboratory temperature for 3.5 hours. Butyryl chloride (0.014 ml.) was added and the mixture was stirred at laboratory temperature for 16 hours, diluted with ethyl acetate (30 ml.) and filtered. The filtrate was washed with water, dried and evaporated to dryness. The residue was purified by chromatography on a silica gel column using a 1:1 v/v mixture of ethyl acetate and toluene as eluant. There was thus obtained as an oil N-n-butyl-11-(3-butyryloxy-17β-hydroxyoestra-1,3,5(10)-trien-7α-yl)-N-methylundecanamide, the structure of which was confirmed by proton magnetic resonance and mass spectroscopy.

Workup

  1. stirringthe mixture was stirred at laboratory temperature for 16 hours
  2. filtrationfiltered
  3. washThe filtrate was washed with water
  4. customdried
  5. customevaporated to dryness
  6. customThe residue was purified by chromatography on a silica gel column
  7. additiona 1:1 v/v mixture of ethyl acetate and toluene as eluant

Sources & evidence

ORD record
ord-84df6cdc30bc45be89305185ef578fd7
Source dataset
uspto-grants-1987_04
Patent number
US04659516

Reaction notes

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