Trifluoroacetic acid → 3-{2-{[(2,5-Dichloro-thiophene-3-carbonyl)-methyl-amino]-methyl}-4-[2-(5-methyl-2-phenyl-oxazol-4-yl)-ethoxy]-phenyl}-propionic acid

HRID 1181077Notes

Reaction equation

HRID 1181077 reaction equation
C([O:5][C:6](=[O:42])[CH2:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][CH2:16][CH2:17][C:18]2[N:19]=[C:20]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[O:21][C:22]=2[CH3:23])=[CH:11][C:10]=1[CH2:30][N:31]([C:33]([C:35]1[CH:39]=[C:38]([Cl:40])[S:37][C:36]=1[Cl:41])=[O:34])[CH3:32])(C)(C)C.C1(OC)C=CC=CC=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[Cl:41][C:36]1[S:37][C:38]([Cl:40])=[CH:39][C:35]=1[C:33]([N:31]([CH2:30][C:10]1[CH:11]=[C:12]([O:15][CH2:16][CH2:17][C:18]2[N:19]=[C:20]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[O:21][C:22]=2[CH3:23])[CH:13]=[CH:14][C:9]=1[CH2:8][CH2:7][C:6]([OH:42])=[O:5])[CH3:32])=[O:34]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acid2×HCID 7519AnisoleHCID 58979258HCID 58979258, compound

Product 1

HCID 179843313-{2-{[(2,5-Dichloro-thiophene-3-carbonyl)-methyl-amino]-methyl}-4-[2-(5-methyl-2-phenyl-oxazol-4-yl)-ethoxy]-phenyl}-propionic acidYield 95%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 3-{2-{[(2,5-dichloro-thiophene-3-carbonyl)-methyl-amino]-methyl}-4-[2-(5-methyl-2-phenyl-oxazol-4-yl)-ethoxy]-phenyl}-propionic acid tert butyl ester (50 mg, 0.079 mmol) in CH2Cl2 (2 mL) was treated with anisole (1.0 mL) then TFA (0.6 mL). The solution was stirred at ambient temperature 2 h, and more TFA (1.0 mL) was added. After 15 min, the reaction was concentrated and co-evaporated with CCl4 (3×). The residue was triturated with hexanes to yield a foam (43 mg, 95%). 1H NMR (400 MHz, CDCl3) δ 2.36 (s, 3H), 2.48 (t, 0.6H, J=7.8 Hz), 2.58 (t, 1.4H, J=7.8 Hz), 2.72 (t, 0.6H, J=7.8 Hz), 2.84 (s, 2H), 2.90 (t, 1.4H, J=7.8 Hz), 2.93 (s, 1H), 2.98 (brs, 2H), 4.17 (t, 2H, J=6.4 Hz), 4.47 (s, 0.6H), 4.71 (s, 1.4H), 6.61 (brs, 0.3H), 6.71-6.76 (m, 2H), 6.79 (s, 0.7H), 7.04 (d, 0.3H, J=8.3 Hz), 7.08 (d, 0.7H, J=8.3 Hz), 7.41-7.43 (m, 3H), 7.94 (brs, 2H).

Workup

  1. waitAfter 15 min
  2. concentrationthe reaction was concentrated
  3. customThe residue was triturated with hexanes

Sources & evidence

ORD record
ord-d718c362391b4a2ba1ac77902b5c4269
Source dataset
uspto-grants-2007_10
Patent number
US07282501B2

Reaction notes

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