4-Toluenesulfonyl chloride → HCID 11338856, compound

HRID 1835039Notes

Reaction equation

HRID 1835039 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]([CH:31]2[CH2:33][CH2:32]2)[C:9]([F:30])([CH:13](O)[CH2:14][C:15]2[CH:20]=[CH:19][C:18]([F:21])=[C:17]([O:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[CH:16]=2)C(O)=O)=[CH:4][CH:3]=1.S(Cl)(C1C=CC(C)=CC=1)(=O)=O>N1C(C)=CC(C)=CC=1C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]([CH:31]2[CH2:33][CH2:32]2)/[C:9](/[F:30])=[CH:13]/[CH2:14][C:15]2[CH:20]=[CH:19][C:18]([F:21])=[C:17]([O:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[CH:16]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 11397324HCID 11397324, compound

Product 1

HCID 11338856HCID 11338856, compoundYield 69.8%

Reagents, catalysts & solvents 1

HCID 79532,4,6-TrimethylpyridineSolvent

Procedure

A solution of crude (2R,3S or 2S,3R)-2-[(S)-(4-chlorophenyl)(cyclopropyl)methyl]-2-fluoro-4-(4-fluoro-3-phenoxyphenyl)-3-hydroxybutanoic acid (Diastereomer E) (0.72 g, 1.5 mmol), tosyl chloride (0.58 g, 3.0 mmol) and collidine (20 ml) is heated at 170° C. for 2 hours. The mixture is concentrated in vacuo and the residue chromatographed on silica gel eluting with ether:hexane (5:95) to yield the title compound as a colorless liquid (0.43 g, 69% from diasteriomer B), [α]D=+35.8 (C=0.0438, CHCl3) which is characterized by 1HNMR and 19FNMR spectral analyses.

Workup

  1. concentrationThe mixture is concentrated in vacuo
  2. customthe residue chromatographed on silica gel eluting with ether:hexane (5:95)

Sources & evidence

ORD record
ord-3b7362b410f64c0c9c1f96adb1225d2a
Source dataset
uspto-grants-2004_08
Patent number
US06770463B2

Reaction notes

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