4-Toluenesulfonyl chloride → HCID 13189269, compound

HRID 434513Notes

Reaction equation

HRID 434513 reaction equation
[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][C@@H:8]1[C@@:41]2([CH3:42])[C:12](=[CH:13][CH2:14][C@@H:15]3[C@@H:40]2[CH2:39][CH2:38][C@@:37]2([CH3:43])[C@H:16]3[CH2:17][CH2:18][C@@H:19]2[C@H:20]([CH2:35][OH:36])[CH2:21][CH2:22][C:23]([F:34])([F:33])[C:24]([O:27][CH:28]([O:30][CH2:31][CH3:32])[CH3:29])([CH3:26])[CH3:25])[CH2:11][C@@H:10]([O:44][CH:45]2[CH2:50][CH2:49][CH2:48][CH2:47][O:46]2)[CH2:9]1.[C:51]1([CH3:61])[CH:56]=[CH:55][C:54]([S:57](Cl)(=[O:59])=[O:58])=[CH:53][CH:52]=1>N1C=CC=CC=1>[CH3:61][C:51]1[CH:56]=[CH:55][C:54]([S:57]([O:36][CH2:35][C@@H:20]([C@@H:19]2[C@:37]3([CH3:43])[C@H:16]([C@H:15]4[C@H:40]([CH2:39][CH2:38]3)[C@:41]3([CH3:42])[C:12]([CH2:11][C@@H:10]([O:44][CH:45]5[CH2:50][CH2:49][CH2:48][CH2:47][O:46]5)[CH2:9][C@@H:8]3[O:7][CH:2]3[CH2:3][CH2:4][CH2:5][CH2:6][O:1]3)=[CH:13][CH2:14]4)[CH2:17][CH2:18]2)[CH2:21][CH2:22][C:23]([F:33])([F:34])[C:24]([O:27][CH:28]([O:30][CH2:31][CH3:32])[CH3:29])([CH3:26])[CH3:25])(=[O:59])=[O:58])=[CH:53][CH:52]=1

Participants

4

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 13189266HCID 13189266, compound

Product 1

HCID 13189269HCID 13189269, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of 2.37 g (0.0033 mol) of [1α,3β]-1,3-bis[(tetrahydro-2H-pyran-2-yl)oxy]-25-(1-ethoxyethoxy)-24,24-difluorocholest-5-en-21-ol, 7 mL of pyridine and 1.27 g (0.0067 mol) of p-toluenesulfonyl chloride was stirred at 0° C. for 18 hr. The mixture was quenched with ice chips. The mixture was then poured into water and extracted with methylene chloride. The organic phase was washed with 10% aqueous sulfuric acid and saturated aqueous sodium bicarbonate solution. The organic layer was dried over anhydrous magnesium sulfate, filtered and evaporated to dryness to yield oily [1α,3β]-1,3-bis[(tetrahydro-2H-pyran-2-yl)oxy]-25-(1-ethoxyethoxy)-24,24-difluorocholest-5-en-21-ol 21-(4-methylbenzenesulfonate), [α]D20 +6° (c 1, CHCl3).

Workup

  1. customThe mixture was quenched with ice chips
  2. additionThe mixture was then poured into water
  3. extractionextracted with methylene chloride
  4. washThe organic phase was washed with 10% aqueous sulfuric acid and saturated aqueous sodium bicarbonate solution
  5. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. customevaporated to dryness

Sources & evidence

ORD record
ord-e8ea24638c9a405da111ceb40e084735
Source dataset
uspto-grants-1983_08
Patent number
US04397847

Reaction notes

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