1,3-Dibromo-5,5-dimethylhydantoin → HCID 131723313, compound

HRID 1816475Notes

Reaction equation

HRID 1816475 reaction equation
[CH3:1][O:2][C:3](=[O:37])[CH2:4][CH2:5][C@H:6]([C@@H:8]1[C@:25]2([CH3:26])[C@H:11]([C@H:12]3[C@H:22]([CH2:23][CH2:24]2)[C@:20]2([CH3:21])[C:15]([C:16]([CH3:36])([CH3:35])[C@@H:17]([O:27][Si:28]([C:31]([CH3:34])([CH3:33])[CH3:32])([CH3:30])[CH3:29])[CH2:18][CH2:19]2)=[CH:14][CH2:13]3)[CH2:10][CH2:9]1)[CH3:7].BrN1C(C)(C)C(=O)N(Br)[C:40]1=[O:41]>C1C=CC=CC=1.CCCCCC>[CH3:1][O:2][C:3](=[O:37])[CH2:4][CH2:5][C@H:6]([C@@H:8]1[C@:25]2([CH3:26])[C@H:11]([C:12]3[C@H:22]([CH2:23][CH2:24]2)[C@:20]2([CH3:21])[C:15]([C:16]([CH3:36])([CH3:35])[C@@H:17]([O:27][Si:28]([C:31]([CH3:34])([CH3:33])[CH3:32])([CH3:29])[CH3:30])[CH2:18][CH2:19]2)=[CH:14][CH:13]=3)[CH2:10][CH2:9]1)[CH3:7].[CH3:40][OH:41]

Participants

5

Reactant 2

HCID 64791,3-Dibromo-5,5-dimethylhydantoinHCID 69412991HCID 69412991, compound

Product 1

HCID 131723313HCID 131723313, compoundYield 106.1%

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 8058HexaneSolvent

Procedure

3β-tert-Butyldimethylsilyloxy-4,4-dimethylchol-5-en-24-oic acid methyl ester (9.75 g) is dissolved in a warm mixture of 122 ml of benzene and 475 ml of n-hexane, 1,3-dibromo-5,5-dimethylhydantoin (3.95 g) is added and the mixture is refluxed for 15 minutes. After cooling (fast) and evaporating to dryness under reduced pressure, 475 ml of α-xylene and 21.7 ml of quinaldine is added and the mixture is refluxed for 1 hour. After aqueous work-up and trituration with methanol 3β-tert-butyldimethylsilyloxy-4,4-dimethylchola-5,7-dien-24-oic acid methyl ester (8.22 g) is isolated. Melting point: 116-124° C. 1H-NMR (CDCl3, 300 MHz): δ=5.88 (1H, m); 5.52 (1H, m); 3.65 (3H, s); 3.32 (1H, m); 0.89 (9H, s); 0.04 (6H, m).

Workup

  1. additionis added
  2. temperaturethe mixture is refluxed for 15 minutes
  3. temperatureAfter cooling (fast)
  4. customevaporating to dryness under reduced pressure, 475 ml of α-xylene and 21.7 ml of quinaldine
  5. additionis added
  6. temperaturethe mixture is refluxed for 1 hour

Sources & evidence

ORD record
ord-9125dc8323254319ba705ec99c282513
Source dataset
uspto-grants-2005_04
Patent number
US06884796B2

Reaction notes

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