Water → HCID 21138129, compound

HRID 651497Notes

Reaction equation

HRID 651497 reaction equation
[C:1](OC(=O)C)(=[O:3])[CH3:2].[C:8]([O:11][C@H:12]1[CH2:17][CH2:16][C@H:15]2[C@H:18]3[C:27]([C@@H:28]([CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][OH:38])[CH2:29][C@:13]12[CH3:14])=[C:26]1[C:21](=[CH:22][C:23](=[O:39])[CH2:24][CH2:25]1)[CH2:20][CH2:19]3)(=[O:10])[CH3:9].O.[Cl-].[NH4+]>CN(C)C1C=CN=CC=1.N1C=CC=CC=1.CO>[C:8]([O:11][C@H:12]1[CH2:17][CH2:16][C@H:15]2[C@H:18]3[C:27]([C@@H:28]([CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][O:38][C:1](=[O:3])[CH3:2])[CH2:29][C@:13]12[CH3:14])=[C:26]1[C:21](=[CH:22][C:23](=[O:39])[CH2:24][CH2:25]1)[CH2:20][CH2:19]3)(=[O:10])[CH3:9]

Participants

8

Reactant 4

HCID 962WaterHCID 7918Acetic AnhydrideHCID 25517Ammonium ChlorideHCID 21138130HCID 21138130, compound

Product 1

HCID 21138129HCID 21138129, compound

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 887MethanolSolventHCID 1049PyridineSolvent

Procedure

3.6 cm3 of acetic anhydride and 95 mg of 4-(dimethylamino) pyridine are added to a solution of 1.4 g of 17beta-(acetyloxy) 11beta-(8-hydroxy octyl)-estra-4,9-dien-3-one (obtained by a similar process to Stage D of the preparation of Example 50 of the European Patent Application EP 384 842) in 10 cm3 of pyridine. The solution is agitated for one hour at ambient temperature, 5 cm3 of water and 5 cm3 of methanol are added, followed by agitation for ten minutes at 0°/+5° C., the whole is poured into a saturated aqueous solution of ammonium chloride, extracted with ethyl acetate, washed with a saturated solution of sodium chloride, dried and evaporated to dryness under reduced pressure after having entrained the pyridine with toluene. 1.61 g of crude product is obtained which is chromatographed on silica, eluant: ethyl acetate-cyclohexane 3-7. In this way 1.28 g of desired product is collected.

Workup

  1. waitfollowed by agitation for ten minutes at 0°
  2. extractionextracted with ethyl acetate
  3. washwashed with a saturated solution of sodium chloride
  4. customdried
  5. customevaporated to dryness under reduced pressure

Sources & evidence

ORD record
ord-582fcbee4cf745b5a050753f056bd5ae
Source dataset
uspto-grants-2001_08
Patent number
US06281204B1

Reaction notes

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