Hydrochloric Acid → HCID 70634905, compound

HRID 328668Notes

Reaction equation

HRID 328668 reaction equation
[C:1]([O:4][CH2:5][C:6](=[O:30])[C@:7]1(O)[C@:24]2([CH3:25])[C@H:10]([C@H:11]3[C@:21]([F:27])([C@@H:22]([Br:26])[CH2:23]2)[C@:19]2([CH3:20])[C:14](=[CH:15][C:16](=[O:28])[CH2:17][CH2:18]2)[CH2:13][CH2:12]3)[CH2:9][CH2:8]1)(=[O:3])[CH3:2].BrN1C(=O)CCC1=O.S(=O)=O.Cl>N1C=CC=CC=1>[C:1]([O:4][CH2:5][C:6](=[O:30])[C:7]1[C@:24]2([CH3:25])[C@H:10]([C@H:11]3[C@:21]([F:27])([C@@H:22]([Br:26])[CH2:23]2)[C@:19]2([CH3:20])[C:14](=[CH:15][C:16](=[O:28])[CH2:17][CH2:18]2)[CH2:13][CH2:12]3)[CH2:9][CH:8]=1)(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 1119Sulfur DioxideHCID 67184N-bromobutanimideHCID 70634275HCID 70634275, compound

Product 1

HCID 70634905HCID 70634905, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent3×

Procedure

A solution of 21-acetyloxy-11β-bromo-9-fluoro-17-hydroxypregn-4-ene-3,20-dione (4.0 g) in pyridine (10 ml) is cooled to 10° C. A solution of N-bromosuccinimide (2.0 g) in pyridine (7.0 ml) is added at 10° C and the mixture is warmed to room temperature and stirred for 10 minutes. It is recooled to 10° C and a solution of sulfur dioxide (2.2 g) in pyridine (10 ml) is added. The mixture is warmed to room temperature and then added slowly, with stirring into 1N hydrochloric acid (300 ml). The title compound is separated and purified.

Workup

  1. customis recooled to 10° C
  2. temperatureThe mixture is warmed to room temperature
  3. additionadded slowly
  4. customThe title compound is separated
  5. custompurified

Sources & evidence

ORD record
ord-95f48ea33e1d4c9cae39607d9d622782
Source dataset
uspto-grants-1977_04
Patent number
US04018757

Reaction notes

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