4-Toluenesulfonyl chloride → HCID 86610071, compound

HRID 1592994Notes

Reaction equation

HRID 1592994 reaction equation
[S:1](Cl)([C:4]1[CH:10]=[CH:9][C:7]([CH3:8])=[CH:6][CH:5]=1)(=[O:3])=[O:2].[F:12][C:13]1[CH:14]=[C:15]([C@@H:20]([C:24]2[CH:29]=[CH:28][C:27]([S:30]([CH3:33])(=[O:32])=[O:31])=[CH:26][CH:25]=2)[CH2:21][CH2:22][OH:23])[CH:16]=[C:17]([F:19])[CH:18]=1>N1C=CC=CC=1>[CH3:8][C:7]1[CH:9]=[CH:10][C:4]([S:1]([O:23][CH2:22][CH2:21][C@@H:20]([C:15]2[CH:16]=[C:17]([F:19])[CH:18]=[C:13]([F:12])[CH:14]=2)[C:24]2[CH:29]=[CH:28][C:27]([S:30]([CH3:33])(=[O:32])=[O:31])=[CH:26][CH:25]=2)(=[O:3])=[O:2])=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 69235746HCID 69235746, compound

Product 1

HCID 86610071HCID 86610071, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent2×

Procedure

Tosyl chloride (3 g) was added portionwise to pyridine (50 ml) at 5° C., followed by a solution of (3R)-3-(3,5-difluorophenyl)-3-[4-(methylsulfonyl)phenyl]propan-1-ol (3.1 g) in pyridine (15 ml) and the resulting mixture was stirred at room temperature for 18 hours. The reaction mixture was poured onto ice/2N HCl and extracted with diethyl ether (×2). The organic extracts were dried and evaporated to dryness to give (3R)-3-(3,5-difluorophenyl)-3-[4-(methylsulfonyl)phenyl]propyl 4-methylbenzenesulfonate as a solid. Yield 2.9 g. NMR (CDCl3): 2.4 (m, 2H), 2.5 (s, 3H), 3.05 (s, 3H), 3.95 (m, 2H), 4.2 (t, 1H), 6.7 9 m, 3H), 7.3 9 m, 4H), 7.75 (d, 2H), 7.85 (d, 2H).

Workup

  1. additionThe reaction mixture was poured onto ice/2N HCl
  2. extractionextracted with diethyl ether (×2)
  3. customThe organic extracts were dried
  4. customevaporated to dryness

Sources & evidence

ORD record
ord-6967d2189cff4b98b0ba7525484736ac
Source dataset
uspto-grants-2007_11
Patent number
US07294636B2

Reaction notes

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