Hydrochloric Acid → HCID 68131244, compound

HRID 1580572Notes

Reaction equation

HRID 1580572 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](OC(=O)C)(=[O:34])[CH3:33].O.Cl>N1C=CC=CC=1>[C:32]([O:19][CH2:18][C:17](=[O:20])[C@:16]1([O:24][C:25](=[O:28])[CH2:26][CH3:27])[C@:21]2([CH3:23])[C@H:13]([C@H:12]3[C@H:3]([C@@H:2]([Cl:1])[CH2:22]2)[C@:4]2([CH3:31])[C:9](=[CH:8][C:7](=[O:30])[CH:6]=[CH:5]2)[CH2:10][CH2:11]3)[CH2:14][C@@H:15]1[CH3:29])(=[O:34])[CH3:33]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 7918Acetic AnhydrideHCID 68131863HCID 68131863, compound

Product 1

HCID 68131244HCID 68131244, 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 treated with acetic anhydride (0.2 ml) at room temperature. After 3 hours water (0.4 ml) was added and the solution was poured into dilute by hydrochloric acid. The precipitated solid was removed by filtration and after drying was recrystallized from methanol to give the title compound, m.p. 212°-213°(K), [α]D + 101.1° (c 0.6 chloroform). λmax 239 nm (ε 16,280) (Found: C, 65.7; H, 7.0; Cl, 6.8. C27H35ClO6 requires C, 66.0; H, 7.2, Cl, 7.2%).

Workup

  1. additionthe solution was poured
  2. customThe precipitated solid was removed by filtration
  3. customafter drying
  4. customwas recrystallized from methanol

Sources & evidence

ORD record
ord-443294c540ae4b0caac21e053593e1a1
Source dataset
uspto-grants-1976_01
Patent number
US03933799

Reaction notes

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