Trifluoroacetic acid → HCID 86722621, compound

HRID 587773Notes

Reaction equation

HRID 587773 reaction equation
C(O)([C:3]([F:6])([F:5])[F:4])=O.Br[C:9]1[CH:26]=[C:25](/[CH:27]=[CH:28]/[CH:29]([C:34]2[CH:39]=[C:38]([Cl:40])[C:37]([Cl:41])=[C:36]([Cl:42])[CH:35]=2)[C:30]([F:33])([F:32])[F:31])[CH:24]=[CH:23][C:10]=1[C:11]([NH:13][CH:14]([CH3:22])[C:15]([O:17]C(C)(C)C)=[O:16])=[O:12]>C(Cl)Cl>[F:31][C:30]([F:33])([F:32])[CH:29]([C:34]1[CH:39]=[C:38]([Cl:40])[C:37]([Cl:41])=[C:36]([Cl:42])[CH:35]=1)/[CH:28]=[CH:27]/[C:25]1[CH:24]=[CH:23][C:10]([C:11]([NH:13][C@H:14]([CH3:22])[C:15]([OH:17])=[O:16])=[O:12])=[C:9]([C:3]([F:6])([F:5])[F:4])[CH:26]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86722622HCID 86722622, compound

Product 1

HCID 86722621HCID 86722621, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

TFA (1 mL) was added to a stirred solution of tert-butyl 2-(2-bromo-4-((E)-4,4,4-trifluoro-3-(3,4,5-trichlorophenyl)but-1-enyl)benzamido)propanoate (1.0 g, 1.63 mmol) in CH2Cl2 (20 mL) at 0° C. and the reaction mixture was stirred at ambient temperature for 18 h. The volatiles were evaporated under vacuum and the residue was triturated with pentane to afford the title compound as brown solid (0.65 g, 67%): 1HNMR (400 MHz, DMSO-d6) δ 12.60 (bs, 1H), 8.82 (d, J=8.0 Hz, 1H), 7.99 (s, 1H), 7.92-7.89 (m, 3H), 7.51 (d, J=8.0 Hz, 1H), 7.08 (dd, J=15.6, 8.8 Hz, 1H), 6.88 (d, J=15.6 Hz, 1H), 4.88-4.83 (m, 1H), 4.41-4.34 (m, 1H), 1.34 (d, J=7.2 Hz, 3H); ESIMS: m/z 545.7 ([M−H]+); IR (KBr) 3410, 3281, 2928, 1728, 1172, 744 cm−1.

Workup

  1. customThe volatiles were evaporated under vacuum
  2. customthe residue was triturated with pentane

Sources & evidence

ORD record
ord-116d48a3b9774a3e923597c4419dd185
Source dataset
uspto-grants-2016_01
Patent number
US09226501B2

Reaction notes

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