1,3-Dibromo-5,5-dimethylhydantoin → HCID 53837977, compound

HRID 2397952Notes

Reaction equation

HRID 2397952 reaction equation
[C:1]([O:4][C@@H:5]1[C@@:33]2([CH3:34])[C:9](=[CH:10][CH2:11][C@@H:12]3[C@@H:32]2[CH2:31][CH2:30][C@@:29]2([CH3:35])[C@H:13]3[CH2:14][CH2:15][C@@H:16]2[C@H:17]([CH3:28])[CH2:18][CH2:19][CH:20]([O:24][C:25](=[O:27])[CH3:26])[CH:21]([CH3:23])[CH3:22])[CH2:8][C@@H:7]([O:36][C:37](=[O:39])[CH3:38])[CH2:6]1)(=[O:3])[CH3:2].BrN1C(C)(C)C(=O)N(Br)C1=O.COP(OC)OC.O[C@@H]1[C@@]2(C)C(=CC[C@@H]3[C@@H]2CC[C@@]2(C)[C@H]3CC[C@@H]2[C@H](C)CCC(OC(=O)C2C=CC=CC=2)C(C)C)C[C@@H](OC(=O)C2C=CC=CC=2)C1>C1(C)C(C)=CC=CC=1.CCCCCC>[C:1]([O:4][C@@H:5]1[C@@:33]2([CH3:34])[C:9](=[CH:10][CH:11]=[C:12]3[C@@H:32]2[CH2:31][CH2:30][C@@:29]2([CH3:35])[C@H:13]3[CH2:14][CH2:15][C@@H:16]2[C@H:17]([CH3:28])[CH2:18][CH2:19][CH:20]([O:24][C:25](=[O:27])[CH3:26])[CH:21]([CH3:23])[CH3:22])[CH2:8][C@@H:7]([O:36][C:37](=[O:39])[CH3:38])[CH2:6]1)(=[O:3])[CH3:2]

Participants

7

Reactant 4

HCID 64791,3-Dibromo-5,5-dimethylhydantoinHCID 8472Trimethyl phosphiteHCID 54039359HCID 54039359, compoundHCID 70634867HCID 70634867, compound

Product 1

HCID 53837977HCID 53837977, compound

Reagents, catalysts & solvents 2

HCID 7237O-XyleneSolvent2×HCID 8058HexaneSolvent

Procedure

150 mg of 1α,3β,24-triacetoxycholest-5-ene was reacted with 45 mg of 1,3-dibromo-5,5-dimethylhydantoine in 3 ml. of n-hexane for 15 minutes under reflux. The reaction mixture was cooled, and the resulting crystals were removed by filtration. The filtrate was concentrated at reduced pressure to afford a yellow oily substance. To this substance was added 1.3 ml. of xylene. The resulting solution was added dropwise over the course of about 15 minutes to a solution of 0.25 ml. of trimethylphosphite in 4 ml. of xylene under reflux, and the reaction was performed for an additional 90 minutes. The reaction mixture was then concentrated at a temperature of less than 75° C. to afford 148 mg of an oily substance. This substance was treated in the same way as in Example 5, (B). The final product showed the same UV, mass, and NMR spectrum data as the 1α,3β,24-triacetoxycholesta-5,7-diene obtained in Example 5, (B).

Workup

  1. temperatureThe reaction mixture was cooled
  2. customthe resulting crystals were removed by filtration
  3. concentrationThe filtrate was concentrated at reduced pressure
  4. customto afford a yellow oily substance
  5. additionTo this substance was added 1.3 ml
  6. additionThe resulting solution was added dropwise over the course of about 15 minutes to a solution of 0.25 ml
  7. concentrationThe reaction mixture was then concentrated at a temperature of less than 75° C.
  8. customto afford 148 mg of an oily substance

Sources & evidence

ORD record
ord-03e5eb7abf974c5eb1af364e61326deb
Source dataset
uspto-grants-1977_05
Patent number
US04022891

Reaction notes

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