Trifluoroacetic acid → 1-(2-Hydroxy-2-(4-(5-(5-phenyl-4-propylisoxazol-3-yl)-1,2,4-oxadiazol-3-yl)phenyl)ethyl)azetidine-3-carboxylic acid

HRID 1948468Notes

Reaction equation

HRID 1948468 reaction equation
[OH:1][CH:2]([C:15]1[CH:20]=[CH:19][C:18]([C:21]2[N:25]=[C:24]([C:26]3[C:30]([CH2:31][CH2:32][CH3:33])=[C:29]([C:34]4[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=4)[O:28][N:27]=3)[O:23][N:22]=2)=[CH:17][CH:16]=1)[CH2:3][N:4]1[CH2:7][CH:6]([C:8]([O:10]C(C)(C)C)=[O:9])[CH2:5]1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[OH:1][CH:2]([C:15]1[CH:16]=[CH:17][C:18]([C:21]2[N:25]=[C:24]([C:26]3[C:30]([CH2:31][CH2:32][CH3:33])=[C:29]([C:34]4[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=4)[O:28][N:27]=3)[O:23][N:22]=2)=[CH:19][CH:20]=1)[CH2:3][N:4]1[CH2:5][CH:6]([C:8]([OH:10])=[O:9])[CH2:7]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 58374129tert-Butyl 1-(2-hydroxy-2-(4-(5-(5-phenyl-4-propylisoxazol-3-yl)-1,2,4-oxadiazol-3-yl)phenyl)ethyl)azetidine-3-carboxylate

Product 1

HCID 509232721-(2-Hydroxy-2-(4-(5-(5-phenyl-4-propylisoxazol-3-yl)-1,2,4-oxadiazol-3-yl)phenyl)ethyl)azetidine-3-carboxylic acidYield 112.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To tert-butyl 1-(2-hydroxy-2-(4-(5-(5-phenyl-4-propylisoxazol-3-yl)-1,2,4-oxadiazol-3-yl)phenyl)ethyl)azetidine-3-carboxylate (8 mg, 0.015 mmol) was added DCM (2 mL) and TFA (2.000 mL). The reaction mixture was stirred 2 hours. Next, the solvent was removed and the remaining contents were freeze dried from MeCN to yield 8 mg of 1-(2-hydroxy-2-(4-(5-(5-phenyl-4-propylisoxazol-3-yl)-1,2,4-oxadiazol-3-yl)phenyl)ethyl)azetidine-3-carboxylic acid as a TFA salt. 1H NMR (400 MHz, DMSO-d6) δ ppm 8.19 (2H, d, J=8.35 Hz), 7.83 (2H, dd, J=8.02, 1.65 Hz), 7.58-7.73 (5H, m), 4.32-4.83 (3H, m), 3.43-4.20 (6H, m), 2.95-3.05 (2H, m), 1.65-1.75 (2H, m), 0.97 (3H, t, J=7.36 Hz). MS (m+1)=475. HPLC Peak RT=3.38 minutes (Analytical Method A). Purity=90%.

Workup

  1. customNext, the solvent was removed
  2. dry with materialdried from MeCN

Sources & evidence

ORD record
ord-4b48b6e63e814567ad02db185261ab63
Source dataset
uspto-grants-2013_03
Patent number
US08399451B2

Reaction notes

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