Sodium Chloride → HCID 15351969, compound

HRID 2185126Notes

Reaction equation

HRID 2185126 reaction equation
[Cl:1]N1C(=O)CCC1=O.[C:9]1([CH2:15][O:16][C:17]2[CH:22]=[CH:21][C:20]([C@H:23]3[CH2:40][C@@:38]4([CH3:39])[C@@H:34]([CH2:35][CH2:36][C:37]4=[O:41])[C@H:33]4[C:24]3=[C:25]3[C:30]([CH2:31][CH2:32]4)=[CH:29][C:28](=[O:42])[CH2:27][CH2:26]3)=[CH:19][CH:18]=2)[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.[Na+].[Cl-].C1CCCCC1>CN(C)C=O>[Cl:1][C:29]1[C:28](=[O:42])[CH2:27][CH2:26][C:25]2[C:30]=1[CH2:31][CH2:32][C@@H:33]1[C:24]=2[C@@H:23]([C:20]2[CH:19]=[CH:18][C:17]([O:16][CH2:15][C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=3)=[CH:22][CH:21]=2)[CH2:40][C@@:38]2([CH3:39])[C@H:34]1[CH2:35][CH2:36][C:37]2=[O:41]

Participants

6

Reactant 4

HCID 5234Sodium ChlorideHCID 8078CyclohexaneHCID 31398ChlorosuccinimideHCID 15351936HCID 15351936, compound

Product 1

HCID 15351969HCID 15351969, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

5.295 g of N-chlorosuccinimide is added at 60° C. under an inert atmosphere to a solution of 13.6 g of 11β-[4-(phenylmethoxy) phenyl]-estra-4,9-diene-3,17-dione in 120 ml of dimethylformamide, agitation is carried out for 10 minutes then the reaction medium is poured into a saturated aqueous solution of NaCl, followed by extraction, washing, drying and evaporating under reduced pressure until the crude product is obtained (m=19.128 g). A second trial is carried out, the crude products are collected and purified by chromatography eluting with an ethyl acetate-cyclohexane mixture 30/70. 23.28 g of expected pure product is obtained. (Rf ACOET/cyclohexane 30/70=0.19). NMR (CDCl3): 0.58 (s): CH3 in position 18; 3.25 (dt): 1H equatorial H6; 4.39 (dl): H11; 5.02 (s): CH2Ph; 6.89: H in ortho position of Ph—O; 7.06: H in meta position of Ph-o; 7.29 to 7.45: aromatic H of CH2—Ph.

Workup

  1. extractionfollowed by extraction
  2. washwashing
  3. customdrying
  4. customevaporating under reduced pressure until the crude product
  5. customis obtained (m=19.128 g)
  6. customthe crude products are collected
  7. custompurified by chromatography
  8. washeluting with an ethyl acetate-cyclohexane mixture 30/70
  9. custom23.28 g of expected pure product is obtained

Sources & evidence

ORD record
ord-ede8b56b86f642fd8abc85a300baab72
Source dataset
uspto-grants-2002_06
Patent number
US06399766B2

Reaction notes

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