Trifluoroacetic acid → HCID 86679835, compound

HRID 1519257Notes

Reaction equation

HRID 1519257 reaction equation
FC(F)(F)C(O)=O.[CH3:8][O:9][C:10]([C:12]1[C:13]([C:31]2[CH:36]=[CH:35][C:34]([C:37]([O:39]C(C)(C)C)=[O:38])=[CH:33][CH:32]=2)=[CH:14][CH:15]=[C:16]([C:18]2[S:19][CH:20]=[C:21]([C:23]3[CH:28]=[CH:27][C:26]([Cl:29])=[C:25]([Cl:30])[CH:24]=3)[N:22]=2)[CH:17]=1)=[O:11]>C(Cl)Cl>[CH3:8][O:9][C:10]([C:12]1[C:13]([C:31]2[CH:36]=[CH:35][C:34]([C:37]([OH:39])=[O:38])=[CH:33][CH:32]=2)=[CH:14][CH:15]=[C:16]([C:18]2[S:19][CH:20]=[C:21]([C:23]3[CH:28]=[CH:27][C:26]([Cl:29])=[C:25]([Cl:30])[CH:24]=3)[N:22]=2)[CH:17]=1)=[O:11]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86679836HCID 86679836, compound2×

Product 1

HCID 86679835HCID 86679835, compoundYield 98.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (8.3 mL, 108 mmol) was added to a solution of 4-[4-(3,4-dichloro-phenyl)-thiazol-2-yl]-biphenyl-2,4′-dicarboxylic acid 4′-tert-butyl ester 2-methyl ester (which may be prepared as described for Intermediate 7; 5.8 g, 10.7 mmol) in CH2Cl2 (25 mL) at 0-5° C. The mixture was allowed to warm to room temperature and stir for 3 h. The resulting solution was concentrated under a stream of nitrogen and then dried under high vacuum to give 4-[4-(3,4-dichloro-phenyl)-thiazol-2-yl]-biphenyl-2,4′-dicarboxylic acid 2-methyl ester (5.1 g, 98%) as a tan solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 13.08 (br s, 1H), ppm 8.49 (s, 1H), 8.42 (s, 1H), 8.35 (s, 1H), 8.30 (d, J=8.0 Hz, 1H), 8.10 (d, J=8.3 Hz, 1H), 8.02 (d, J=8.0 Hz, 2H), 7.77 (d, J=8.5 Hz, 1H), 7.66 (d, J=8.0 Hz, 1H), 7.49 (d, J=8.3 Hz, 2H).

Workup

  1. concentrationThe resulting solution was concentrated under a stream of nitrogen
  2. customdried under high vacuum

Sources & evidence

ORD record
ord-563c3187952a402f9bbd9236a1fd1191
Source dataset
uspto-grants-2015_07
Patent number
US09073881B2

Reaction notes

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