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Hydrochloric Acid → 17alpha-Chloroacetoxy-pregn-4-ene-3,20-dione

HRID 1447579
Notes
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Reaction equation

HRID 1447579 reaction equation
F[C:2](F)(F)[C:3]([O:5]C(=O)C(F)(F)F)=O.[OH:14][C@:15]1([C@:35]2([CH3:36])[C@H:21]([C@H:22]3[C@H:32]([CH2:33][CH2:34]2)[C@:30]2([CH3:31])[C:25](=[CH:26][C:27](=[O:37])[CH2:28][CH2:29]2)[CH2:24][CH2:23]3)[CH2:20][CH2:19]1)[C:16](=[O:18])[CH3:17].C1(C)C=CC=CC=1.[ClH:45]>CO>[Cl:45][CH2:2][C:3]([O:14][C@:15]1([C@:35]2([CH3:36])[C@H:21]([C@H:22]3[C@H:32]([CH2:33][CH2:34]2)[C@:30]2([CH3:31])[C:25](=[CH:26][C:27](=[O:37])[CH2:28][CH2:29]2)[CH2:24][CH2:23]3)[CH2:20][CH2:19]1)[C:16](=[O:18])[CH3:17])=[O:5]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 1140TolueneHCID 623817-HydroxyprogesteroneHCID 9845Trifluoroacetic anhydride

Product 1

HCID 8673671717alpha-Chloroacetoxy-pregn-4-ene-3,20-dione

Reagents, catalysts & solvents 1

HCID 887
Methanol
Solvent

Conditions

Temperature
60 °C

Procedure

A mixture of 3-/N,N-bis(2-chloroethyl)amino/-4-methylbenzoic acid (27.6 g) and trifluoroacetic anhydride (21.0 g) is heated under stirring at 60° C. for 15 min. To the mixture 17α-hydroxypregn-4-ene-3,20-dione (16.5 g) is added and the mixture is heated under stirring at 80° C. for 5 h. Toluene (150 ml) is added, the solution is filtered, and to the filtrate chloroform (200 ml) is added. After washing with H2O and aq. NaHCO3, drying, and evaporation an oil is obtained, to which a mixture of methanol (300 ml) and conc. HCl (3 ml) is added. After 16 h at room temperature the solution is evaporated and the residue chromatographed on a silica gel column using toluene/ethyl acetate (2:1) as eluent. The eluate fraction having Rf =0.40 gives 17α-/3-(N,N-bis(2-chloroethyl)amino)-4-methylbenzoyloxy/pregn-4-ene-3,20-dione (1, 6.8 g, m.p. 170°-1° C.).

Workup

  1. temperatureis heated
  2. temperaturethe mixture is heated
  3. stirringunder stirring at 80° C. for 5 h
  4. filtrationthe solution is filtered
  5. additionto the filtrate chloroform (200 ml) is added
  6. washAfter washing with H2O and aq. NaHCO3
  7. customdrying
  8. customevaporation an oil
  9. customis obtained, to which
  10. additionis added
  11. customAfter 16 h at room temperature the solution is evaporated
  12. customthe residue chromatographed on a silica gel column

Sources & evidence

ORD record
ord-72c0cc4976964636a99400b0f198c648
Source dataset
uspto-grants-1979_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04177269

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes