Hydrochloric Acid → HCID 71573271, compound

HRID 532141Notes

Reaction equation

HRID 532141 reaction equation
C(OC[C:6]1[CH:11]=[C:10]([C:12]2[CH2:16][C:15]([C:21]3[CH:26]=[C:25]([Cl:27])[CH:24]=[C:23]([Cl:28])[CH:22]=3)([C:17]([F:20])([F:19])[F:18])[O:14][N:13]=2)[CH:9]=[CH:8][C:7]=1[B:29]1[O:33]C(C)(C)[C:31](C)(C)[O:30]1)(=O)C.O[Li].O.Cl>C1COCC1.O.CC(=O)OCC.Cl.CCO.O>[Cl:27][C:25]1[CH:26]=[C:21]([C:15]2([C:17]([F:19])([F:20])[F:18])[O:14][N:13]=[C:12]([C:10]3[CH:9]=[CH:8][C:7]4[B:29]([OH:33])[O:30][CH2:31][C:6]=4[CH:11]=3)[CH2:16]2)[CH:22]=[C:23]([Cl:28])[CH:24]=1

Participants

8

Reactant 3

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 86685044HCID 86685044, compound

Product 1

HCID 71573271HCID 71573271, compoundYield 27%

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 8857Ethyl AcetateSolventHCID 21881883Oxolane--water (1/1)SolventHCID 21887872Ethanol hydrochlorideSolvent

Procedure

A mixture of 5-(5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl)-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzyl acetate (50 mg, 0.09 mmol) and LiOH H2O (15 mg, 0.36 mmol) in THF—H2O (1 mL/0.2 mL) was stirred at rt for 1 h and diluted with EA (2 mL). The organic phase was dried over MgSO4, filtered and concentrated under reduced pressure to give a residue that was dissolved in HCl-EtOH (4 N, 5 mL) and H2O (0.3 mL). The mixture was stirred at 35° C. for 20 h. To it was added conc HCl (1.7 mL) and the reaction mixture was stirred at 60° C. for 20 h. The mixture was cooled to rt, concentrated under reduced pressure. The residue was purified by preparative TLC to give the desired title compound (10 mg; yield 27%) as a white solid. 1H NMR (400 MHz, CDCl3): δ 7.81 (d, J=6.8 Hz, 1 H), 7.68 (s, 1 H), 7.63 (d, J=8.0 Hz, 1 H), 7.51 (s, 2 H), 7.43 (d, J=1.2 Hz, 1 H), 5.13 (s, 2 H), 4.12 (m, 1 H), 3.74 (m, 1 H) ppm; MS: m/z=416 (M+1, ESI+).

Workup

  1. dry with materialThe organic phase was dried over MgSO4
  2. filtrationfiltered
  3. concentrationconcentrated under reduced pressure
  4. customto give a residue that
  5. stirringThe mixture was stirred at 35° C. for 20 h
  6. stirringthe reaction mixture was stirred at 60° C. for 20 h
  7. temperatureThe mixture was cooled to rt
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was purified by preparative TLC

Sources & evidence

ORD record
ord-70a8e58e7c4d4d8a90fd532c6ba2a00f
Source dataset
uspto-grants-2014_10
Patent number
US08853186B2

Reaction notes

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