Water → HCID 69737675, compound

HRID 967723Notes

Reaction equation

HRID 967723 reaction equation
[Cl:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH:7]1[CH2:24][C@@:22]2([CH3:23])[C@@H:18]([CH2:19][CH:20]=[C:21]2[O:25]C(=O)C)[C@H:17]2[C@H:8]1[C:9]1[CH:10]=[CH:11][C:12]([O:29][C:30](=[O:32])[CH3:31])=[CH:13][C:14]=1[CH2:15][CH2:16]2.C([O-])(=O)C.[Na+].[Br:38]N1C(=O)CCC1=O.O>CN(C)C=O>[C:30]([O:29][C:12]1[CH:11]=[CH:10][C:9]2[C@@H:8]3[C@H:17]([C@H:18]4[C@@:22]([CH2:24][CH:7]3[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][Cl:1])([CH3:23])[C:21](=[O:25])[CH:20]([Br:38])[CH2:19]4)[CH2:16][CH2:15][C:14]=2[CH:13]=1)(=[O:32])[CH3:31]

Participants

6

Reactant 4

HCID 962WaterHCID 67184N-bromobutanimideHCID 517045Sodium AcetateHCID 69738763HCID 69738763, compound

Product 1

HCID 69737675HCID 69737675, compoundYield 228.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 6.2 g of 11-(5-chloropentyl)-3,17-diacetoxy-estra-1,3,5(10),16-tetraene in 95 ml of dimethylformamide is mixed at 0° C. first with 9.05 ml of sodium acetate solution (10%) and then with 2.6 g of N-bromosuccinimide, and it is stirred for one hour. Then, it is mixed with water, extracted with ethyl acetate, washed with sodium sulfate solution as well as common salt solution, dried on sodium sulfate and evaporated to the dry state in a vacuum. 15.3 g of crude 3-acetoxy-16-bromo-11-(5-chloropentyl)-estra-1,3,5(10)-trien-17-one is obtained.

Workup

  1. extractionextracted with ethyl acetate
  2. washwashed with sodium sulfate solution as well as common salt solution
  3. customdried on sodium sulfate
  4. customevaporated to the dry state in a vacuum

Sources & evidence

ORD record
ord-f62c48d69aeb4ebabd2b5809cecb5043
Source dataset
uspto-grants-2005_10
Patent number
US06956031B2

Reaction notes

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