4-Toluenesulfonyl chloride → HCID 86586579, compound

HRID 895851Notes

Reaction equation

HRID 895851 reaction equation
[C:1]1([CH3:11])[CH:6]=[CH:5][C:4]([S:7](Cl)(=[O:9])=[O:8])=[CH:3][CH:2]=1.[C:12]([O:20][C@H:21]1[CH2:41][CH2:40][C@@:39]2([CH3:42])[C:23](=[CH:24][CH:25]=[C:26]3[C@@H:38]2[CH2:37][CH2:36][C@@:35]2([CH3:43])[C@H:27]3[CH2:28][CH2:29][C@@H:30]2[C@H:31]([CH3:34])[CH2:32][OH:33])[C:22]1([CH3:45])[CH3:44])(=[O:19])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>N1C=CC=CC=1>[C:12]([O:20][C@H:21]1[CH2:41][CH2:40][C@@:39]2([CH3:42])[C:23](=[CH:24][CH:25]=[C:26]3[C@@H:38]2[CH2:37][CH2:36][C@@:35]2([CH3:43])[C@H:27]3[CH2:28][CH2:29][C@@H:30]2[C@@H:31]([CH2:32][O:33][S:7]([C:4]2[CH:5]=[CH:6][C:1]([CH3:11])=[CH:2][CH:3]=2)(=[O:9])=[O:8])[CH3:34])[C:22]1([CH3:44])[CH3:45])(=[O:19])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

4

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 69788666HCID 69788666, compound

Product 1

HCID 86586579HCID 86586579, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent2×

Procedure

A solution of 0.573 g toluene-4-sulfonylchloride in 4 ml pyridine was added drop by drop to a solution of 0.926 g (20S)-4,4,20-trimethyl-pregna-5,7-dien-3β,21-diol 3-benzoate in 15 ml pyridine while cooling on an ice-bath. The reaction mixture was stirred for 1 h at 0-3□C. and overnight at room temperature. The reaction mixture was poured into ice-water and extracted with ethyl acetate. The organic layers were combined, washed with 1N hydrochloric acid, saturated sodium hydrogencarbonate solution and brine. The organic layer was dried over sodium sulfate, filtered and concentrated under reduced pressure to give 1.0 g of (20S)-4,4-dimethyl-20-[((toluene-4-sulfonyl)oxy)methyl]-pregna-5,7-dien-3β-ol benzoate which could be further purified by crystallization from methanol.

Workup

  1. temperaturewhile cooling on an ice-bath
  2. customovernight
  3. customat room temperature
  4. extractionextracted with ethyl acetate
  5. washwashed with 1N hydrochloric acid, saturated sodium hydrogencarbonate solution and brine
  6. dry with materialThe organic layer was dried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-44c4952a085149a0834e692fd880a48a
Source dataset
uspto-grants-2005_07
Patent number
US06916921B2

Reaction notes

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