Water → HCID 70447820, compound

HRID 543009Notes

Reaction equation

HRID 543009 reaction equation
[C:1](OC(=O)C)(=[O:3])[CH3:2].[CH2:8]([N:12]([CH3:45])[C:13](=[O:44])[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][C@@H:24]1[CH2:41][C:40]2[CH:39]=[C:38]([OH:42])[CH:37]=[CH:36][C:35]=2[C@@H:34]2[C@@H:25]1[C@H:26]1[C@@:30]([CH2:32][CH2:33]2)([CH3:31])[C@@H:29]([OH:43])[CH2:28][CH2:27]1)[CH2:9][CH2:10][CH3:11].[OH2:46].[C:47]1([CH3:53])C=CC=CC=1>N1C=CC=CC=1>[CH2:8]([N:12]([CH3:45])[C:13](=[O:44])[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][C@@H:24]1[CH2:41][C:40]2[CH:39]=[C:38]([O:42][C:1](=[O:3])[CH3:2])[CH:37]=[CH:36][C:35]=2[C@@H:34]2[C@@H:25]1[C@H:26]1[C@@:30]([CH2:32][CH2:33]2)([CH3:31])[C@@H:29]([O:43][C:47](=[O:46])[CH3:53])[CH2:28][CH2:27]1)[CH2:9][CH2:10][CH3:11]

Participants

6

Reactant 4

HCID 962WaterHCID 1140TolueneHCID 7918Acetic AnhydrideHCID 104772(7alpha,17beta)-N-Butyl-3,17-dihydroxy-N-methylestra-1,3,5(10)-triene-7-undecanamide

Product 1

HCID 70447820HCID 70447820, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Acetic anhydride (0.2 ml.) was added to a stirred solution of N-n-butyl-11-(3,17β-dihydroxyoestra-1,3,5(10)-trien-7α-yl)-N-methylundecanamide (Example 2; 0.052 g.) in pyridine (0.5 ml.) and the mixture was stirred at laboratory temperature for 16 hours. Water (0.1 ml.) was added and then toluene was added and distilled off until the mixture was free of acetic acid. The residue was purified by chromatography on a silica gel column using a 4:1 v/v mixture of toluene and ethyl acetate as eluant, and there was thus obtained as an oil N-n-butyl-11-(3,17β-diacetoxyoestra-1,3,5(10) -trien-7α-yl)-N-methylundecanamide, the structure of which was confirmed by proton magnetic resonance and mass spectroscopy.

Workup

  1. distillationdistilled off until the mixture
  2. customThe residue was purified by chromatography on a silica gel column
  3. additiona 4:1 v/v mixture of toluene and ethyl acetate as eluant

Sources & evidence

ORD record
ord-993684539559460bb1d01d53b34f6fae
Source dataset
uspto-grants-1987_04
Patent number
US04659516

Reaction notes

Loading…