1,3-Dibromo-5,5-dimethylhydantoin → HCID 13826525, compound

HRID 980069Notes

Reaction equation

HRID 980069 reaction equation
[C:1]([O:4][C@@H:5]1[C@@:31]2([CH3:32])[C:9](=[CH:10][CH2:11][C@@H:12]3[C@@H:30]2[CH2:29][CH2:28][C@@:27]2([CH3:33])[C@H:13]3[CH2:14][CH2:15][C@@H:16]2[C@H:17]([CH3:26])[CH2:18][CH2:19][C@@H:20]([F:25])[C:21]([OH:24])([CH3:23])[CH3:22])[CH2:8][C@@H:7]([O:34][C:35](=[O:37])[CH3:36])[CH2:6]1)(=[O:3])[CH3:2].C(=O)(O)[O-].[Na+].[Br:43]N1C(C)(C)C(=O)N(Br)C1=O>CCCCCC>[C:1]([O:4][C@@H:5]1[C@@:31]2([CH3:32])[C:9](=[CH:10][CH:11]([Br:43])[C@@H:12]3[C@@H:30]2[CH2:29][CH2:28][C@@:27]2([CH3:33])[C@H:13]3[CH2:14][CH2:15][C@@H:16]2[C@H:17]([CH3:26])[CH2:18][CH2:19][C@@H:20]([F:25])[C:21]([OH:24])([CH3:22])[CH3:23])[CH2:8][C@@H:7]([O:34][C:35](=[O:37])[CH3:36])[CH2:6]1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 64791,3-Dibromo-5,5-dimethylhydantoinHCID 516892Sodium BicarbonateHCID 13826522HCID 13826522, compound

Product 1

HCID 13826525HCID 13826525, compound

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 0.520 g. (0.0010 mole) of [1α,3β,24R]-24-fluorocholest-5-en-1,3,25-triol 1,3-diacetate, 0.45 g. of sodium bicarbonate, 0.192 g. (0.00066 mole) of 1,3-dibromo-5,5-dimethylhydantoin and 25 ml. of hexane was heated at reflux (80° C.) for 1 hr and cooled. The mixture was filtered and the solids were triturated with hexane and filtered. The filtrates were evaporated to dryness to yield [1α,3β,7ξ,24R]-7-bromo-24-fluorcholest-5-en-1,3,25-triol 1,3-diacetate.

Workup

  1. additionA mixture of 0.520 g
  2. temperaturecooled
  3. filtrationThe mixture was filtered
  4. customthe solids were triturated with hexane
  5. filtrationfiltered
  6. customThe filtrates were evaporated to dryness

Sources & evidence

ORD record
ord-f787365a798e46c3a1d071cc566932fb
Source dataset
uspto-grants-1987_01
Patent number
US04634692

Reaction notes

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