Hydrochloric Acid → HCID 68064146, compound

HRID 572593Notes

Reaction equation

HRID 572593 reaction equation
[OH:1][CH2:2][CH:3]([NH:32][CH2:33][C:34]([O:36]C(C)(C)C)=[O:35])[C:4]1[CH:9]=[CH:8][C:7]([C:10]2[N:14]=[C:13]([C:15]3[CH:20]=[CH:19][C:18]([C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=4[CH3:27])=[C:17]([C:28]([F:31])([F:30])[F:29])[CH:16]=3)[O:12][N:11]=2)=[CH:6][CH:5]=1.Cl>O1CCOCC1>[OH:1][CH2:2][CH:3]([NH:32][CH2:33][C:34]([OH:36])=[O:35])[C:4]1[CH:5]=[CH:6][C:7]([C:10]2[N:14]=[C:13]([C:15]3[CH:20]=[CH:19][C:18]([C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=4[CH3:27])=[C:17]([C:28]([F:29])([F:30])[F:31])[CH:16]=3)[O:12][N:11]=2)=[CH:8][CH:9]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 66652776HCID 66652776, compound

Product 1

HCID 68064146HCID 68064146, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
80 °C

Procedure

To tert-butyl N-[2-hydroxy-1-(4-{5-[2′-methyl-2-(trifluoromethyl)biphenyl-4-yl]-1,2,4-oxadiazol-3-yl}phenyl)ethyl]glycinate (0.200 g; 0.13 mmol) was added HCl solution in dioxane (4 M; 4 mL) and the reaction mixture stirred 80° C. for 1 hour. The reaction mixture was allowed to cool and the solvent evaporated in vacuo. The residue was purified by preparative HPLC to afford the title compound. 1H NMR: (CDCl3, 400 MHz) δ 8.57 (1H, d, J=1.2 Hz), 8.54-8.52 (1H, m), 8.14 (2H, d, J=8 Hz), 7.70 (1H, d, J=8 Hz), 7.63 (2H, d, J=8.4 Hz), 7.44-7.38 (2H, m), 7.34-7.30 (1H, m), 7.21-7.20 (1H, m), 3.94-3.91 (1H, m), 3.65-3.56 (1H, m), 3.52-3.47 (1H, m), 3.20 (1H, d, J=16.8 Hz), 3.06 (1H, d, J=16.8 Hz), 2.06 (3H, s). LC/MS (Method B): 496 (M+H)+. HPLC (Method D) Rt 3.04 min (Purity: 94.9%).

Workup

  1. temperatureto cool
  2. customthe solvent evaporated in vacuo
  3. customThe residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-6f1d566aed2c4b6aa35cedcc58f57ca4
Source dataset
uspto-grants-2015_05
Patent number
US09029405B2

Reaction notes

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