Water → HCID 68132151, compound

HRID 1580576Notes

Reaction equation

HRID 1580576 reaction equation
[C:1]([O:4][C@:5]1([C@:26]2([CH3:27])[C@H:12]([C@H:13]3[C@H:23]([C@@H:24]([Cl:28])[CH2:25]2)[C@:21]2([CH3:22])[C:16](=[CH:17][C:18](=[O:29])[CH:19]=[CH:20]2)[CH2:15][CH2:14]3)[CH2:11][C@@H:10]1[CH3:30])[C:6](=[O:9])[CH2:7][OH:8])(=[O:3])[CH3:2].[C:31](Cl)(=[O:34])[CH2:32][CH3:33].O>N1C=CC=CC=1.Cl>[C:1]([O:4][C@:5]1([C@:26]2([CH3:27])[C@H:12]([C@H:13]3[C@H:23]([C@@H:24]([Cl:28])[CH2:25]2)[C@:21]2([CH3:22])[C:16](=[CH:17][C:18](=[O:29])[CH:19]=[CH:20]2)[CH2:15][CH2:14]3)[CH2:11][C@@H:10]1[CH3:30])[C:6](=[O:9])[CH2:7][O:8][C:31](=[O:34])[CH2:32][CH3:33])(=[O:3])[CH3:2]

Participants

6

Reactant 3

HCID 962WaterHCID 62324Propionyl chlorideHCID 68131415HCID 68131415, compound

Product 1

HCID 68132151HCID 68132151, compound

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 1049PyridineSolvent

Procedure

A solution of 17-acetoxy-11β-chloro-21-hydroxy-16β-methylpregna-1,4-diene-3,20-dione (67 mg.) in pyridine (1 ml.) at 0° was treated with propionyl chloride (0.03 ml.). After one hour, a little water was added and the solution was diluted with dilute hydrochloric acid. The precipitated solid was collected and recrystallized from methanol to give the title compound, m.p. 213°-215° (K), [α]D + 108.4° (c 0.6, chloroform) λmax 240 nm (ε 15,760) (Found: C, 65.9; H, 7.2. C27H35Cl O6 requires C, 66.0; H, 7.2).

Workup

  1. customThe precipitated solid was collected
  2. customrecrystallized from methanol

Sources & evidence

ORD record
ord-6b63c8c39dd942d9b43c8679abc4c504
Source dataset
uspto-grants-1976_01
Patent number
US03933799

Reaction notes

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