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Acetic Acid → HCID 86738653, compound

HRID 2199084
Notes
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Reaction equation

HRID 2199084 reaction equation
C([O:4][C@H:5]1[CH2:22][C@@:20]2([CH3:21])[C@@H:16]([CH2:17][CH2:18][C:19]2([S:25][CH2:26][CH3:27])[S:23][CH3:24])[C@H:15]2[C@@:6]1([F:30])[C@:7]1([CH3:29])[C:12]([CH2:13][CH2:14]2)=[CH:11][C:10](=[O:28])[CH:9]=[CH:8]1)(=O)C.[OH-].[Na+].C(O)(=O)C>CO.O1CCCC1>[CH2:26]([S:25][C:19]1([S:23][CH3:24])[CH2:18][CH2:17][C@H:16]2[C@H:15]3[C@:6]([F:30])([C@@H:5]([OH:4])[CH2:22][C@:20]12[CH3:21])[C@:7]1([CH3:29])[C:12](=[CH:11][C:10](=[O:28])[CH:9]=[CH:8]1)[CH2:13][CH2:14]3)[CH3:27]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 14798Sodium HydroxideHCID 86738652HCID 86738652, compound

Product 1

HCID 86738653HCID 86738653, compoundYield 97.8%

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent
HCID 8028
Tetrahydrofuran
Solvent

Procedure

A solution of 11β-acetyloxy-17-(ethylthio)-9-fluoro-17-(methylthio)androsta-1,4-diene-3-one (620 mg) in a mixture of methanol (20 ml) and tetrahydrofuran (10 ml) is stirred under nitrogen with 3 M aqueous sodium hydroxide (1.5 ml). After eighteen hours, a slight excess of acetic acid is added. The mixture is concentrated in vacuo, diluted with water and extracted with chloroform. The chloroform solution is washed with water, dried, evaporated and chromatographed over a column of silica gel (10 g) eluting the column successively with chloroform-hexane (4:1), chloroform and chloroform-ethyl acetate (95:5) to isolate the title compound (550 mg). Crystallization of this from ethyl acetate-hexane and drying (110° C., 0.3 mm of Hg, 7 hours) gives the analytical specimen, melting point 275° C., dec. (contracts from approximately 200° C., discoloration starts from approximately 220° C. and becomes deeper until spontaneous melting at 275° C. with decomposition) with consistent spectral data. The nmr spectrum shows that this is an essentially 1:1 mixture of the two 17-stereoisomers.

Workup

  1. waitAfter eighteen hours
  2. concentrationThe mixture is concentrated in vacuo
  3. additiondiluted with water
  4. extractionextracted with chloroform
  5. washThe chloroform solution is washed with water
  6. customdried
  7. customevaporated
  8. customchromatographed over a column of silica gel (10 g)
  9. washeluting the column successively with chloroform-hexane (4:1), chloroform and chloroform-ethyl acetate (95:5)

Sources & evidence

ORD record
ord-3d5dcdbd7ec74af8aa0fd70bae64fde1
Source dataset
uspto-grants-1982_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04361559

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes