Trifluoroacetic acid → HCID 22280103, compound

HRID 1063745Notes

Reaction equation

HRID 1063745 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][C:21]([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:20][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:21]2[CH:20]=[CH:19][C:18]([CH2:17][S:16][C:13]3[CH:14]=[CH:15][C:6]([O:5][CH2:4][C:3]([OH:36])=[O:2])=[C:7]4[C:12]=3[O:11][CH2:10][CH2:9][CH2:8]4)=[CH:23][CH:22]=2)=[CH:31][CH:30]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 253877Potassium BromideHCID 20827102HCID 20827102, compound

Product 1

HCID 22280103HCID 22280103, compound

Reagents, catalysts & solvents 1

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

Procedure

The title compound was prepared in the manner analogous to Example 1 using 83A. mp 143-144° C.; HPLC: area %=96.02, r.t.=3.770 min, γ=214 nm, mobile phase=acetonitrile/water w/0.10% TFA; IR (KBr) cm−1: 3042, 2581, 1739, 1714, 1325, 1116; 400 MHz 1H NMR (DMSO-d6): δ 12.95 (br(s), 1H), 7.66-7.74 (m, 2H), 7.56-7.63 (m, 2H); 7.10-7.17 (m, 2H), 6.92 (d, 1H, J=8.7 Hz), 6.83-6.89 (m, 2H), 6.26 (d, 1H, J=8.5 Hz), 5.13 (s, 2H), 4.58 (s, 2H), 4.08 (t, 2H, J=4.8 Hz), 3.90 (s, 2H), 2.55 (t, 2H, J=6.5 Hz), 1.83 (pentet, 2H); MS m/z 503 (M−1). Anal. Calc'd for C26H23F3O5S: C, 61.90; H, 4.60. found: C, 61.41; H, 4.50.

Sources & evidence

ORD record
ord-5d7f14942bc44b69b30daa8a84a3886f
Source dataset
uspto-grants-2005_11
Patent number
US06964983B2

Reaction notes

Loading…