Trifluoroacetic acid → HCID 89620441, compound

HRID 1775872Notes

Reaction equation

HRID 1775872 reaction equation
[Br:1][C:2]1[CH:3]=[N:4][C:5]([C:8]2[CH:13]=[CH:12][C:11]([CH2:14][C@H:15]([NH:23][C:24]([C:26]3[S:27][C:28]([C:31]([CH3:34])([CH3:33])[CH3:32])=[CH:29][CH:30]=3)=[O:25])[C:16]([O:18]C(C)(C)C)=[O:17])=[CH:10][CH:9]=2)=[N:6][CH:7]=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[Br:1][C:2]1[CH:7]=[N:6][C:5]([C:8]2[CH:9]=[CH:10][C:11]([CH2:14][C@H:15]([NH:23][C:24]([C:26]3[S:27][C:28]([C:31]([CH3:34])([CH3:33])[CH3:32])=[CH:29][CH:30]=3)=[O:25])[C:16]([OH:18])=[O:17])=[CH:12][CH:13]=2)=[N:4][CH:3]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86689679HCID 86689679, compound

Product 1

HCID 89620441HCID 89620441, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirring solution of tert-butyl (S)-3-(4-(5-bromopyrimidin-2-yl)phenyl)-2-(5-(tert-butyl)thiophene-2-carboxamido)propanoate INT-17 (15.7 g, 28.8 mmol) in DCM (30 mL) was treated with TFA (30.0 g, 263.1 mmol). The reaction mixture was stirred at room temperature for 18 hours to complete. The solvent was evaporated and then co-evaporated with toluene (3×20 mL) to remove trace TFA. The compound was dried under vacuum overnight to afford 13.7 g (97%) of (S)-3-(4-(5-bromopyrimidin-2-yl)phenyl)-2-(5-(tert-butyl)thiophene-2-carboxamido)propanoic acid as powder. LCMS-ESI (m/z) calculated for C22H22BrN3O3S: 487.1. found 488.1 [M+H]+, tR=2.55 min. (Method 16). 1H NMR (400 MHz, DMSO) δ 9.05 (d, J=5.0 Hz, 2H), 8.64 (d, J=8.4 Hz, 1H), 8.25 (d, J=8.1 Hz, 2H), 7.62 (d, J=3.8 Hz, 1H), 7.45 (d, J=8.2 Hz, 2H), 6.92 (d, J=3.8 Hz, 2H), 4.64 (td, J=10.5, 4.5 Hz, 1H), 3.26 (dd, J=13.8, 4.4 Hz, 1H), 3.11 (dd, J=13.7, 10.7 Hz, 1H), 1.32 (s, 9H).

Workup

  1. customThe solvent was evaporated
  2. customto remove trace TFA
  3. customThe compound was dried under vacuum overnight

Sources & evidence

ORD record
ord-0252714d66084ff8a28a1536e79212d8
Source dataset
uspto-grants-2016_02
Patent number
US09260427B2

Reaction notes

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