Hydrochloric Acid → HCID 68131133, compound

HRID 1580573Notes

Reaction equation

HRID 1580573 reaction equation
[Cl:1][C@H:2]1[CH2:22][C@@:21]2([CH3:23])[C@@H:13]([CH2:14][C@H:15]([CH3:29])[C@:16]2([O:24][C:25](=[O:28])[CH2:26][CH3:27])[C:17](=[O:20])[CH2:18][OH:19])[C@H:12]2[C@H:3]1[C@:4]1([CH3:31])[C:9]([CH2:10][CH2:11]2)=[CH:8][C:7](=[O:30])[CH:6]=[CH:5]1.[C:32](Cl)(=[O:35])[CH2:33][CH3:34].O.Cl>N1C=CC=CC=1>[Cl:1][C@H:2]1[CH2:22][C@@:21]2([CH3:23])[C@@H:13]([CH2:14][C@H:15]([CH3:29])[C@:16]2([O:24][C:25](=[O:28])[CH2:26][CH3:27])[C:17](=[O:20])[CH2:18][O:19][C:32](=[O:35])[CH2:33][CH3:34])[C@H:12]2[C@H:3]1[C@:4]1([CH3:31])[C:9]([CH2:10][CH2:11]2)=[CH:8][C:7](=[O:30])[CH:6]=[CH:5]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 62324Propionyl chlorideHCID 68131863HCID 68131863, compound

Product 1

HCID 68131133HCID 68131133, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of 11β-chloro-21-hydroxy-16β-methyl-17-propionyloxypregna-1,4-diene-3,20-dione(75 mg) in pyridine (1 ml) was cooled to 0° and treated with stirring with propionyl chloride (0.04 ml). After 90 minutes a little water was added and the solution poured into dilute hydrochloric acid. The precipitated solid was removed by filtration and recrystallized from methanol to give the title compound, m.p. 220°-222° (K), [α]D + 105° (c 0.6, chloroform) λmax 240nm (ε 15,060) (Found C, 65.9; H, 7.2; Cl, 6.7. C28H37ClO6 requires C, 65.7; H, 7.55; Cl, 7.0%).

Workup

  1. additiontreated
  2. customThe precipitated solid was removed by filtration
  3. customrecrystallized from methanol

Sources & evidence

ORD record
ord-6420b95e9cd14a08b65a22c9c852bf04
Source dataset
uspto-grants-1976_01
Patent number
US03933799

Reaction notes

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