4-Toluenesulfonyl chloride → HCID 12790113, compound

HRID 1701492Notes

Reaction equation

HRID 1701492 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:15][C@@H:16]1[C@@:36]2([CH3:37])[C:20](=[CH:21][CH2:22][C@@H:23]3[C@@H:35]2[CH2:34][CH2:33][C@@:32]2([CH3:38])[C@H:24]3[CH2:25][CH2:26][C@@H:27]2[C@H:28]([CH3:31])[CH2:29][OH:30])[CH2:19][C@@H:18]([O:39][C:40](=[O:42])[CH3:41])[CH2:17]1)(=[O:14])[CH3:13]>N1C=CC=CC=1>[C:12]([O:15][C@@H:16]1[C@@:36]2([CH3:37])[C:20](=[CH:21][CH2:22][C@@H:23]3[C@@H:35]2[CH2:34][CH2:33][C@@:32]2([CH3:38])[C@H:24]3[CH2:25][CH2:26][C@@H:27]2[C@H:28]([CH3:31])[CH2:29][O:30][S:7]([C:4]2[CH:5]=[CH:6][C:1]([CH3:11])=[CH:2][CH:3]=2)(=[O:9])=[O:8])[CH2:19][C@@H:18]([O:39][C:40](=[O:42])[CH3:41])[CH2:17]1)(=[O:14])[CH3:13]

Participants

4

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 12790110HCID 12790110, compound

Product 1

HCID 12790113HCID 12790113, compoundYield 73.7%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent2×

Procedure

A solution of 55.1 mg of p-toluenesulphonyl chloride in 0.2 ml. of dry pyridine was added at 0° C. to a solution of 100 mg of (20S)-1α,3β-diacetoxy-21-hydroxy-20-methyl-pregn-5-ene in 0.5 ml. of dry pyridine. After standing at 0° C. for 6 hours, the mixture was poured on to ice-water and extracted with ether. The extract was washed successively with 2-N hydrochloric acid, water, saturated sodium bicarbonate solution and water. The residue obtained after drying over sodium sulphate and concentration was chromatographed on 3.5 g of silica gel using hexane/ether (4:1) for the elution, there being obtained 100 mg of uniform (20S)-1α,3β-diacetoxy-20-methyl-21-(p-toluene-sulphonyloxy)-pregn-5-ene. After recrystallisation from ether, the product melted at 168°-170° C.; [α]D =-20.8° (c=0.5 in chloroform).

Workup

  1. extractionextracted with ether
  2. washThe extract was washed successively with 2-N hydrochloric acid, water, saturated sodium bicarbonate solution and water
  3. customThe residue obtained
  4. dry with materialafter drying over sodium sulphate and concentration
  5. customwas chromatographed on 3.5 g of silica gel
  6. washfor the elution, there

Sources & evidence

ORD record
ord-4f57c2fde9614ebe82c21bd3b0d61b87
Source dataset
uspto-grants-1980_03
Patent number
US04193921

Reaction notes

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