Trifluoroacetic acid → {8-[3-(4-Trifluoromethyl-benzyloxy)-benzylsulfanyl]-chroman-5-yloxy}-acetic acid

HRID 1063747Notes

Reaction equation

HRID 1063747 reaction equation
C[O:2][C:3](=[O:36])[CH2:4][O:5][C:6]1[CH:15]=[CH:14][C:13]([S:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([O:24][CH2:25][C:26]3[CH:31]=[CH:30][C:29]([C:32]([F:35])([F:34])[F:33])=[CH:28][CH:27]=3)[CH:19]=2)=[C:12]2[C:7]=1[CH2:8][CH2:9][CH2:10][O:11]2.C(O)(C(F)(F)F)=O.[K+].[Br-]>C(#N)C.O>[F:35][C:32]([F:33])([F:34])[C:29]1[CH:28]=[CH:27][C:26]([CH2:25][O:24][C:20]2[CH:19]=[C:18]([CH:23]=[CH:22][CH:21]=2)[CH2:17][S:16][C:13]2[CH:14]=[CH:15][C:6]([O:5][CH2:4][C:3]([OH:36])=[O:2])=[C:7]3[C:12]=2[O:11][CH2:10][CH2:9][CH2:8]3)=[CH:31][CH:30]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 253877Potassium BromideHCID 20827100{8-[3-(4-Trifluoromethyl-benzyloxy)-benzylsulfanyl]-chroman-5-yloxy}-acetic acid methyl ester

Product 1

HCID 22280110{8-[3-(4-Trifluoromethyl-benzyloxy)-benzylsulfanyl]-chroman-5-yloxy}-acetic acid

Reagents, catalysts & solvents 1

HCID 18373917Acetonitrile--water (1/1)Solvent

Procedure

The title compound was prepared in the manner analogous to Example 1 using 84A. mp 113-115° C.; HPLC: area %=97.30, r.t.=3.140 min, γ=214 nm, mobile phase=acetonitrile/water w/0.10% TFA; IR (KBr) cm−1: 2952, 2577, 1742, 1582, 1323, 1120; 400 MHz 1H NMR (DMSO-d6): δ 87.67-7.74 (m, 2H), 7.56-7.63 (m, 2H); 7.13 (t, 1H, J=7.8 Hz), 6.76-6.93 (m, 4H), 6.22 (d, 1H, J=8.7 Hz), 5.08 (s, 2H), 4.45 (s, 2H), 4.08 (t, 2H, J=4.8 Hz), 3.91 (s, 2H), 2.54 (t, 2H, J=6.6 Hz), 1.82 (pentet, 2H); MS m/z 505 (M+1). Anal. Calc'd for C26H23F3O5S: C, 61.90; H, 4.60. found: C, 61.49; H, 4.44.

Sources & evidence

ORD record
ord-6e51013f098d4461bae196cb8f0fb45a
Source dataset
uspto-grants-2005_11
Patent number
US06964983B2

Reaction notes

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