(-)-3-Hydroxytetrahydrofuran → (R)-5-(4-chlorophenyl)-6-(tetrahydrofuran-3-yloxy)nicotinic acid

HRID 1025999Notes

Reaction equation

HRID 1025999 reaction equation
Cl[C:2]1[N:7]=[CH:6][C:5]([C:8]([OH:10])=[O:9])=[CH:4][C:3]=1[C:11]1[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][CH:12]=1.[O:18]1[CH2:22][CH2:21][C@@H:20]([OH:23])[CH2:19]1>>[Cl:17][C:14]1[CH:15]=[CH:16][C:11]([C:3]2[C:2]([O:23][C@@H:20]3[CH2:21][CH2:22][O:18][CH2:19]3)=[N:7][CH:6]=[C:5]([CH:4]=2)[C:8]([OH:10])=[O:9])=[CH:12][CH:13]=1

Participants

3

Reactant 2

HCID 641512(-)-3-HydroxytetrahydrofuranHCID 866191836-Chloro-5-(4-chlorophenyl)-3-pyridinecarboxylic acid

Product 1

HCID 66678800(R)-5-(4-chlorophenyl)-6-(tetrahydrofuran-3-yloxy)nicotinic acid

Procedure

The title compound was synthesized in analogy to Example CI using 6-chloro-5-(4-chlorophenyl)-3-pyridinecarboxylic acid (CAN 1012792-56-1) and (3R)-tetrahydro-3-furanol (CAN 86087-24-3) as starting materials; LC-MS (UV peak area/ESI) 88.1%, 318.1 (M−H)−.

Sources & evidence

ORD record
ord-fe315881cf274dae83e6aada64a8c16d
Source dataset
uspto-grants-2014_05
Patent number
US08729105B2

Reaction notes

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