Trifluoroacetic acid → Trifluoroacetic acid

HRID 1804505Notes

Reaction equation

[CH2:1]([C:5]1[C:6]([C:13]2[O:17][N:16]=[C:15]([C:18]3[CH:35]=[CH:34][C:21]([CH2:22][N:23]4[CH2:26][CH:25]([C:27]([O:29]C(C)(C)C)=[O:28])[CH2:24]4)=[CH:20][CH:19]=3)[N:14]=2)=[N:7][O:8][C:9]=1[CH2:10][CH2:11][CH3:12])[CH:2]([CH3:4])[CH3:3].[C:36]([OH:42])([C:38]([F:41])([F:40])[F:39])=[O:37]>>[CH2:1]([C:5]1[C:6]([C:13]2[O:17][N:16]=[C:15]([C:18]3[CH:19]=[CH:20][C:21]([CH2:22][N:23]4[CH2:26][CH:25]([C:27]([OH:29])=[O:28])[CH2:24]4)=[CH:34][CH:35]=3)[N:14]=2)=[N:7][O:8][C:9]=1[CH2:10][CH2:11][CH3:12])[CH:2]([CH3:4])[CH3:3].[C:36]([OH:42])([C:38]([F:41])([F:40])[F:39])=[O:37]

Participants

Reactant 2

HCID 6422Trifluoroacetic acid

HCID 58537195HCID 58537195, compound

Product 2

HCID 6422Trifluoroacetic acidYield 88%

HCID 46846914HCID 46846914, compound

Procedure

A solution of tert-butyl 1-(4-(5-(4-isobutyl-5-propylisoxazol-3-yl)-1,2,4-oxadiazol-3-yl)benzyl)azetidine-3-carboxylate (21 mg, 0.044 mmol) in TFA (0.5 mL) was allowed to stand at rt for 2.5 hr. The volatiles were removed in vacuo and the residue was triturated with Et2O and dried to afford 1-(4-(5-(4-isobutyl-5-propylisoxazol-3-yl)-1,2,4-oxadiazol-3-yl)benzyl)azetidine-3-carboxylic acid, TFA (21 mg, 0.038 mmol, 88% yield) as a light yellow glassy solid. HPLC retention time=3.20 minutes (YMC Combi 4.6×50 mm S-5 ODS column) eluting with 10-90% aqueous methanol+0.2% phosphoric acid over a 4 minute gradient. MS: (M+H)=425.20. 1H NMR (400 MHz, MeOD) δ ppm 0.96 (d, J=6.5 Hz, 6H) 1.03 (t, J=7.3 Hz, 3H) 1.75-1.86 (m, 2H) 1.94 (m, 1H) 2.68 (d, J=7.3 Hz, 2H) 2.85 (t, J=7.5 Hz, 2H) 3.61-3.71 (m, 1H) 4.29-4.40 (m, 4H) 4.50 (s, 2H) 7.68 (d, J=8.0 Hz, 2H) 8.24 (d, J=8.3 Hz, 2H).

Workup

customThe volatiles were removed in vacuo
customthe residue was triturated with Et2O
customdried

Sources & evidence

ORD record: ord-afa66b82e39747fb8b158427e36662fc
Source dataset: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08354398B2

Reaction notes

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