Benzoyl chloride → HCID 70447030, compound

HRID 543007Notes

Reaction equation

HRID 543007 reaction equation
[C:1](Cl)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:10]([N:14]([CH3:47])[C:15](=[O:46])[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][C@@H:26]1[CH2:43][C:42]2[CH:41]=[C:40]([OH:44])[CH:39]=[CH:38][C:37]=2[C@@H:36]2[C@@H:27]1[C@H:28]1[C@@:32]([CH2:34][CH2:35]2)([CH3:33])[C@@H:31]([OH:45])[CH2:30][CH2:29]1)[CH2:11][CH2:12][CH3:13].C(=O)(O)[O-].[Na+]>CC(C)=O>[CH2:10]([N:14]([CH3:47])[C:15](=[O:46])[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][C@@H:26]1[CH2:43][C:42]2[CH:41]=[C:40]([O:44][C:1](=[O:8])[C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)[CH:39]=[CH:38][C:37]=2[C@@H:36]2[C@@H:27]1[C@H:28]1[C@@:32]([CH2:34][CH2:35]2)([CH3:33])[C@@H:31]([OH:45])[CH2:30][CH2:29]1)[CH2:11][CH2:12][CH3:13]

Participants

5

Reactant 3

HCID 7412Benzoyl chlorideHCID 104772(7alpha,17beta)-N-Butyl-3,17-dihydroxy-N-methylestra-1,3,5(10)-triene-7-undecanamideHCID 516892Sodium Bicarbonate

Product 1

HCID 70447030HCID 70447030, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
0 °C

Procedure

Aqueous N-sodium hydroxide solution (0.15 ml.) and benzoyl chloride (0.023 ml.) were successively added at 0° C. to a stirred solution of N-n-butyl-N-methyl-11-(3,17β-dihydroxyoestra-1,3,5(10)-trien-7α-yl)undecanamide (Example 2; 0.06 g.) in acetone (1 ml.) and the mixture was stirred at 0° C. for 30 minutes and poured into saturated aqueous sodium bicarbonate solution (10 ml.). The mixture was extracted three times with diethyl ether (15 ml. each time) and the combined extracts were washed with water (3 ml.), dried and evaporated to dryness. The residue was purified by chromatography on a silica gel column using a 3:2 v/v mixture of toluene and ethyl acetate as eluant. There was thus obtained as an oil N-n-butyl-N-methyl-11-(3-benzoyloxy-17β-hydroxyoestra-1,3,5(10)-trien-7α-yl)undecanamide, the structure of which was confirmed by proton magnetic resonance and mass spectroscopy.

Workup

  1. extractionThe mixture was extracted three times with diethyl ether (15 ml
  2. washeach time) and the combined extracts were washed with water (3 ml.)
  3. customdried
  4. customevaporated to dryness
  5. customThe residue was purified by chromatography on a silica gel column
  6. additiona 3:2 v/v mixture of toluene and ethyl acetate as eluant

Sources & evidence

ORD record
ord-8b17cf1c80174837a593fa4e4e0776e2
Source dataset
uspto-grants-1987_04
Patent number
US04659516

Reaction notes

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