Hydrochloric Acid → HCID 68132423, compound

HRID 1580575Notes

Reaction equation

HRID 1580575 reaction equation
[C:1](OC(=O)C)(=[O:3])[CH3:2].[Cl:8][C@H:9]1[CH2:29][C@@:28]2([CH3:30])[C@@H:20]([CH2:21][C@H:22]([CH3:37])[C@:23]2([O:31][C:32](=[O:36])[CH:33]([CH3:35])[CH3:34])[C:24](=[O:27])[CH2:25][OH:26])[C@H:19]2[C@H:10]1[C@:11]1([CH3:39])[C:16]([CH2:17][CH2:18]2)=[CH:15][C:14](=[O:38])[CH:13]=[CH:12]1.O.Cl>N1C=CC=CC=1>[C:1]([O:26][CH2:25][C:24](=[O:27])[C@:23]1([O:31][C:32](=[O:36])[CH:33]([CH3:35])[CH3:34])[C@:28]2([CH3:30])[C@H:20]([C@H:19]3[C@H:10]([C@@H:9]([Cl:8])[CH2:29]2)[C@:11]2([CH3:39])[C:16](=[CH:15][C:14](=[O:38])[CH:13]=[CH:12]2)[CH2:17][CH2:18]3)[CH2:21][C@@H:22]1[CH3:37])(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 7918Acetic AnhydrideHCID 18595306HCID 18595306, compound

Product 1

HCID 68132423HCID 68132423, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Acetic anhydride (0.22 ml.) was added to a solution of 11β-chloro-21-hydroxy-17-isobutyryloxy-16β-methylpregna-1,4-diene-3,20 dione (71 mg.) in pyridine (1 ml.) at room temperature. After 3.5 hours, a little water was added and the solution was poured into dilute hydrochloric acid. Filtration of the precipitated solid and crystallization from methanol afforded the title compound, m.p. 204°-205° (K), [α]D + 95.2 (c 0.6 chloroform) λmax 240 nm (ε 15,450) (Found: C, 67.05; H, 7.4; Cl, 7.05, C28H37Cl O6 requires C, 66.6; H, 7.4; Cl, 7.0%).

Workup

  1. filtrationFiltration of the precipitated solid and crystallization from methanol

Sources & evidence

ORD record
ord-4643f46e449f4b3d96f9821056cb3d47
Source dataset
uspto-grants-1976_01
Patent number
US03933799

Reaction notes

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