Trifluoroacetic acid → 2-[2-[[2-(4-Chlorophenyl)-4-methylthiazole-5-carbonyl]aminomethyl]morpholin-4-yl]benzoic acid

HRID 602210Notes

Reaction equation

HRID 602210 reaction equation
FC(F)(F)C(O)=O.[Cl:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[S:16][C:17]([C:21]([NH:23][CH2:24][CH:25]3[O:30][CH2:29][CH2:28][N:27]([C:31]4[CH:43]=[CH:42][CH:41]=[CH:40][C:32]=4[C:33]([O:35]C(C)(C)C)=[O:34])[CH2:26]3)=[O:22])=[C:18]([CH3:20])[N:19]=2)=[CH:11][CH:10]=1>ClCCl>[Cl:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[S:16][C:17]([C:21]([NH:23][CH2:24][CH:25]3[O:30][CH2:29][CH2:28][N:27]([C:31]4[CH:43]=[CH:42][CH:41]=[CH:40][C:32]=4[C:33]([OH:35])=[O:34])[CH2:26]3)=[O:22])=[C:18]([CH3:20])[N:19]=2)=[CH:11][CH:10]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 58992641tert-Butyl 2-[2-[[2-(4-chlorophenyl)-4-methylthiazole-5-carbonyl]aminomethyl]morpholin-4-yl]benzoate

Product 1

HCID 589927032-[2-[[2-(4-Chlorophenyl)-4-methylthiazole-5-carbonyl]aminomethyl]morpholin-4-yl]benzoic acidYield 78%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (1 mL) was added to tert-butyl 2-[2-[[2-(4-chlorophenyl)-4-methylthiazole-5-carbonyl]aminomethyl]morpholin-4-yl]benzoate (113 mg, 0.214 mmol) in dichloromethane (1 mL). The mixture was stirred at room temperature for 2 hours. Subsequently, the solvent was removed and a 1 mol/L aqueous potassium hydroxide solution was added to the residue to make it basic. The mixture was then made acidic by the addition of 2 mol/L hydrochloric acid. The crystallized powdery product was collected by filtration and washed with water to give 78.2 mg (78%) of the desired compound as a colorless powder.

Workup

  1. customSubsequently, the solvent was removed
  2. additiona 1 mol/L aqueous potassium hydroxide solution was added to the residue
  3. additionmade acidic by the addition of 2 mol/L hydrochloric acid
  4. filtrationThe crystallized powdery product was collected by filtration
  5. washwashed with water

Sources & evidence

ORD record
ord-c06b8362a2084885a5f20c9c710a9bf6
Source dataset
uspto-grants-2011_03
Patent number
US07902367B2

Reaction notes

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