Trifluoroacetic acid → HCID 90418705, compound

HRID 2177265Notes

Reaction equation

HRID 2177265 reaction equation
[Cl:1][C:2]1[C:6]([CH2:7][O:8][C:9]2[C:14]([F:15])=[CH:13][C:12]([CH2:16][CH2:17][C:18]([O:20]CC)=[O:19])=[CH:11][C:10]=2[F:23])=[C:5]([C:24]2[CH:29]=[CH:28][C:27]([CH2:30][CH3:31])=[CH:26][CH:25]=2)[S:4][N:3]=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[Cl:1][C:2]1[C:6]([CH2:7][O:8][C:9]2[C:14]([F:15])=[CH:13][C:12]([CH2:16][CH2:17][C:18]([OH:20])=[O:19])=[CH:11][C:10]=2[F:23])=[C:5]([C:24]2[CH:25]=[CH:26][C:27]([CH2:30][CH3:31])=[CH:28][CH:29]=2)[S:4][N:3]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 90417976HCID 90417976, compound

Product 1

HCID 90418705HCID 90418705, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
25 °C

Procedure

Into a 50-mL round-bottom flask, was placed ethyl 3-(4-[[3-chloro-5-(4-ethylphenyl)-1,2-thiazol-4-yl]methoxy]-3,5-difluorophenyl)propanoate (20 mg, 0.04 mmol, 1.00 equiv, 90%), TFA (0.5 mL), CH2Cl2 (2 mL). The resulting solution was stirred overnight at 25° C. The resulting mixture was concentrated under vacuum. The crude product (2 mL) was purified by Prep-HPLC with the following conditions: Column, SunFire Prep C18, Sum, 19*100 mm; mobile phase, Water of 0.05% TFA and CH3CN (40% CH3CN up to 100% in 6 min, hold 100% in 2 min, down to 40% in 0.1 min, hold 40% in 1.9 min); Detector, UV 220&254 nm. This resulted in 10 mg (59%) of 3-(4-[[3-chloro-5-(4-ethylphenyl)-1,2-thiazol-4-yl]methoxy]-3,5-difluorophenyl)propanoic acid as a brown solid. 1H NMR (400 MHz, CD3OD) δ 7.49 (d, J=8.0 Hz, 2H), 7.38 (d, J=8.0 Hz, 2H), 6.83 (d, J=9.2 Hz, 2H), 5.10 (s, 2H), 2.87 (t, J=7.2 Hz, 2H), 2.75 (q, J=7.2, 15.2 Hz, 2H), 2.61 (t, J=7.6 Hz, 2H), 1.30 (t, J=7.6 Hz, 3H). Mass spectrum (ESI, m/z): Calcd. for C21H18ClF2NO3S, 438.1 (M+H). found 438.2.

Workup

  1. customInto a 50-mL round-bottom flask, was placed
  2. concentrationThe resulting mixture was concentrated under vacuum
  3. customThe crude product (2 mL) was purified by Prep-HPLC with the following conditions
  4. waitmobile phase, Water of 0.05% TFA and CH3CN (40% CH3CN up to 100% in 6 min
  5. customin 2 min
  6. waitdown to 40% in 0.1 min
  7. customin 1.9 min
  8. customThis resulted in 10 mg (59%) of 3-(4-[[3-chloro-5-(4-ethylphenyl)-1,2-thiazol-4-yl]methoxy]-3,5-difluorophenyl)propanoic acid as a brown solid

Sources & evidence

ORD record
ord-4b3c8da303b24665ad47e8fda6080815
Source dataset
uspto-grants-2015_06
Patent number
US09067898B1

Reaction notes

Loading…