Trifluoroacetic acid → Trifluoroacetic acid

HRID 77174Notes

Reaction equation

HRID 77174 reaction equation
[OH:1][CH:2]([C:16]1[CH:21]=[CH:20][C:19]([C:22]2[N:26]=[C:25]([C:27]3[O:31][N:30]=[C:29]([C:32]4[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=4)[C:28]=3[C:38]([F:41])([F:40])[F:39])[O:24][N:23]=2)=[CH:18][CH:17]=1)[C:3]([NH:5][CH2:6][CH2:7][NH:8]C(=O)OC(C)(C)C)=[O:4].[C:42]([OH:48])([C:44]([F:47])([F:46])[F:45])=[O:43]>ClCCl>[NH2:8][CH2:7][CH2:6][NH:5][C:3](=[O:4])[CH:2]([OH:1])[C:16]1[CH:21]=[CH:20][C:19]([C:22]2[N:26]=[C:25]([C:27]3[O:31][N:30]=[C:29]([C:32]4[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=4)[C:28]=3[C:38]([F:41])([F:40])[F:39])[O:24][N:23]=2)=[CH:18][CH:17]=1.[C:42]([OH:48])([C:44]([F:47])([F:46])[F:45])=[O:43]

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 53495534(R/S)-tert-butyl 2-(2-hydroxy-2-(4-(5-(3-phenyl-4-(trifluoromethyl)isoxazol-5-yl)-1,2,4-oxadiazol-3-yl)phenyl)acetamido)ethylcarbamate

Product 2

HCID 6422Trifluoroacetic acidYield 83.5%HCID 53495536HCID 53495536, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(R/S)-tert-Butyl 2-(2-hydroxy-2-(4-(5-(3-phenyl-4-(trifluoromethyl)isoxazol-5-yl)-1,2,4-oxadiazol-3-yl)phenyl)acetamido)ethylcarbamate (Example 51, 80 mg, 0.139 mmol) was dissolved in dichloromethane (5 mL). TFA (1 mL, 12.98 mmol) was added. The reaction mixture was stirred for 30 min. All solvent was removed to provide (R/S)-N-(2-aminoethyl)-2-hydroxy-2-(4-(5-(3-phenyl-4-(trifluoromethyl)isoxazol-5-yl)-1,2,4-oxadiazol-3-yl)phenyl)acetamide, TFA (70 mg, 0.116 mmol, 83% yield): LCMS=474.1 [M+H]+; 1H NMR (400 MHz, methanol-d4) δ ppm 8.62 (1 H, t, J=5.93 Hz), 8.19 (2 H, d, J=8.35 Hz), 7.55-7.76 (7 H, m), 5.20 (1 H, s), 3.39-3.64 (2 H, m), 3.07 (2 H, t, J=6.15 Hz); HPLC peak RT=6.3 min (Method A).

Workup

  1. customAll solvent was removed

Sources & evidence

ORD record
ord-eea2c9e9f1fc4af98dfa158abc6c27aa
Source dataset
uspto-grants-2014_09
Patent number
US08835470B2

Reaction notes

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