1-(3,5-Difluorophenyl)ethan-1-ol → (S)-2-(2,6-difluoro-4-(1-hydroxyethyl)phenyl)thiazole-4-carboxylic acid

HRID 521907Notes

Reaction equation

HRID 521907 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([CH:8]([OH:10])[CH3:9])[CH:5]=[C:4]([F:11])[C:3]=1[C:12]1[S:13][CH:14]=[C:15]([C:17]([OH:19])=[O:18])[N:16]=1.FC1C=C(C(O)C)C=C(F)C=1.FC1C=C(C(O)C)C=C(F)C=1B1OC(C)(C)C(C)(C)O1.FC1C=C([C@@H](O)C)C=C(F)C=1>>[F:1][C:2]1[CH:7]=[C:6]([C@@H:8]([OH:10])[CH3:9])[CH:5]=[C:4]([F:11])[C:3]=1[C:12]1[S:13][CH:14]=[C:15]([C:17]([OH:19])=[O:18])[N:16]=1

Participants

5

Reactant 4

HCID 27823261-(3,5-Difluorophenyl)ethan-1-olHCID 40786925(S)-1-(3,5-difluorophenyl)ethanolHCID 867138511-(3,5-Difluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)ethanolHCID 867138522-(2,6-Difluoro-4-(1-hydroxyethyl)phenyl)thiazole-4-carboxylic acid

Product 1

HCID 86713857(S)-2-(2,6-difluoro-4-(1-hydroxyethyl)phenyl)thiazole-4-carboxylic acid

Procedure

Following the procedure of Intermediate 109, replacing 1-(3,5-difluorophenyl)ethanol in step 1 (Intermediate 106) with (S)-1-(3,5-difluorophenyl)ethanol (commercial source).

Sources & evidence

ORD record
ord-b918590eba4e4d699d1d61101af089b7
Source dataset
uspto-grants-2016_05
Patent number
US09328106B2

Reaction notes

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