Hydrochloric Acid → HCID 57965497, compound

HRID 1695548Notes

Reaction equation

HRID 1695548 reaction equation
[CH3:1][C@H:2]1[C@:27]([OH:35])(C(COC(C)=O)=O)[C@:26]2([CH3:36])[C@H:4]([C@H:5]3[C@H:23]([C@@H:24]([OH:37])[CH2:25]2)[C@:22]2([CH3:38])[C:8](=[CH:9][C:10]4[N:14]([C:15]5[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=5)[N:13]=[CH:12][C:11]=4[CH2:21]2)[C:7]([CH3:39])=[CH:6]3)[CH2:3]1.[OH-:40].[Na+].Cl.[CH3:43][OH:44]>>[OH:35][C@@:27]1([C:43]([OH:44])=[O:40])[C@:26]2([CH3:36])[C@H:4]([C@H:5]3[C@H:23]([C@@H:24]([OH:37])[CH2:25]2)[C@@:22]2([CH3:38])[CH2:21][C:11]4[CH:12]=[N:13][N:14]([C:15]5[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=5)[C:10]=4[CH:9]=[C:8]2[C:7]([CH3:39])=[CH:6]3)[CH2:3][C@H:2]1[CH3:1]

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 887Methanol2×HCID 14798Sodium HydroxideHCID 66249Cortivazol

Product 1

HCID 57965497HCID 57965497, compound

Procedure

In a 50 mL round-bottomed flask was dissolved (11β,16α)-21-(Acetyloxy)-11,17-dihydroxy-6,16-dimethyl-2′-phenyl-2′H-pregna-2,4,6-trieno[3,2-c]pyrazol-20-one (also known as Cortivazol) (0.1 g, 0.19 mmol) in MeOH (10 mL) to give a colorless solution. 1M sodium hydroxide (1.2 mL, 1.20 mmol) was added, and the mixture was stirred in an open flask overnight. The solution was acidified by the addition of 1M HCl (1.3 ml), MeOH was removed in vacuo after which the product precipitated as a white solid which was filtered, washed with water and dried in air on the sinter to give 85 mg of the desired product as a white solid. APCI-MS m/z: 475 [MH+].

Workup

  1. customto give a colorless solution
  2. customwas removed in vacuo after which the product
  3. customprecipitated as a white solid which
  4. filtrationwas filtered
  5. washwashed with water
  6. customdried in air on the sinter

Sources & evidence

ORD record
ord-21948844c2574cd19d08c21b903131fa
Source dataset
uspto-grants-2012_04
Patent number
US08163724B2

Reaction notes

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