Water → HCID 22896177, compound

HRID 2120552Notes

Reaction equation

HRID 2120552 reaction equation
[OH:1][CH2:2][CH2:3][CH2:4][C:5]1[CH:10]=[CH:9][C:8]([C@H:11]2[CH2:28][C@@:26]3([CH3:27])[C@@H:22]([CH2:23][CH2:24][C:25]3=O)[C@H:21]3[C:12]2=[C:13]2[C:18]([CH2:19][CH2:20]3)=[CH:17][C:16](=[O:30])[CH2:15][CH2:14]2)=[CH:7][CH:6]=1.[Cl:31]N1C(=O)CCC1=O.O>CN(C=O)C>[Cl:31][C:17]1[C:16](=[O:30])[CH2:15][CH2:14][C:13]2[C:18]=1[CH2:19][CH2:20][C@@H:21]1[C:12]=2[C@@H:11]([C:8]2[CH:7]=[CH:6][C:5]([CH2:4][CH2:3][CH2:2][OH:1])=[CH:10][CH:9]=2)[CH2:28][C@@:26]2([CH3:27])[C@H:22]1[CH2:23][CH2:24][CH2:25]2

Participants

5

Reactant 3

HCID 962WaterHCID 31398ChlorosuccinimideHCID 22896174HCID 22896174, compound

Product 1

HCID 22896177HCID 22896177, compoundYield 74.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 11.9 g of 11β-[4-(3-hydroxypropyl)phenyl]-estra-4.9-diene-3.17-dione prepared to preparation 1 in 100 ml of DMF, under inert atmosphere and at 60° C., 4.93 g of N-chloro succinimide is added and stirred for 10 mn at this temperature. It is poured into water, drawn off, washed, dried, evaporated under reduced pressure until 16.2 g of raw expected product is obtained that is purified by chromatography by eluting with the compound CH2Cl2/Acetone 85/15. 9.34 g of pure expected product is obtained.

Workup

  1. washwashed
  2. customdried
  3. customevaporated under reduced pressure until 16.2 g of raw expected product
  4. customis obtained
  5. customthat is purified by chromatography
  6. washby eluting with the compound CH2Cl2/Acetone 85/15

Sources & evidence

ORD record
ord-3ae4a71e093946d68bab75452b62aee2
Source dataset
uspto-grants-2004_02
Patent number
US06693090B2

Reaction notes

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