Hydrochloric Acid → HCID 16730181, compound

HRID 545587Notes

Reaction equation

HRID 545587 reaction equation
[F:1][C:2]([F:50])([F:49])[C:3]1[CH:4]=[C:5]([CH:42]=[C:43]([C:45]([F:48])([F:47])[F:46])[CH:44]=1)[CH2:6][N:7]([CH2:12][C:13]1[CH:18]=[C:17]([C:19]([F:22])([F:21])[F:20])[CH:16]=[CH:15][C:14]=1[C:23]1[CH:24]=[C:25]([C:31]2[CH:36]=[CH:35][C:34]([C:37]([O:39]C)=[O:38])=[CH:33][C:32]=2[CH3:41])[CH:26]=[CH:27][C:28]=1[O:29][CH3:30])[C:8]([O:10][CH3:11])=[O:9].O.[OH-].[Li+].O.Cl>[Cl-].[Na+].O.O1CCOCC1>[F:1][C:2]([F:49])([F:50])[C:3]1[CH:4]=[C:5]([CH:42]=[C:43]([C:45]([F:47])([F:48])[F:46])[CH:44]=1)[CH2:6][N:7]([CH2:12][C:13]1[CH:18]=[C:17]([C:19]([F:21])([F:22])[F:20])[CH:16]=[CH:15][C:14]=1[C:23]1[CH:24]=[C:25]([C:31]2[CH:36]=[CH:35][C:34]([C:37]([OH:39])=[O:38])=[CH:33][C:32]=2[CH3:41])[CH:26]=[CH:27][C:28]=1[O:29][CH3:30])[C:8]([O:10][CH3:11])=[O:9]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 168937Lithium hydroxide, monohydrateHCID 16730253HCID 16730253, compound

Product 1

HCID 16730181HCID 16730181, compound

Reagents, catalysts & solvents 2

HCID 312751,4-DioxaneSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

Methyl 2″-{[[3,5-bis(trifluoromethyl)benzyl] (methoxycarbonyl)amino]methyl}-4′-methoxy-2-methyl-4″-(trifluoromethyl)-1,1′:3′,1″-terphenyl-4-carboxylate (34.7 mg, 0.0486 mmol), lithium hydroxide monohydrate (10 mg, 0.238 mmol), water (0.4 mL) and 1,4-dioxane (1 mL) were stirred at room temperature for 5.5 hours to complete the reaction. Crude mixture was acidified with HCl (aq, 1N, 6 mL). The resulting mixture was worked up with brine and extracted with ethyl acetate. The combined extracts were back-washed with water. The resulting organic layer was dried over Na2SO4, filtered and evaporated in vacuo to afford a clear oil. The resulting oil was purified on SiO2 to afford as a clear glass 2″-{[[3,5-bis(trifluoromethyl)benzyl] (methoxycarbonyl)amino]methyl}-4′-methoxy-2-methyl-4″-(trifluoromethyl)-1,1′:3′,1″-terphenyl-4-carboxylic acid. LCMS calc.=699.17; found=700.29 (M+1)+. 1H NMR (CDCl3, 500 MHz) δ 8.01 (s, 1H), 7.95 (d, J=7.5 Hz, 1H), 7.72 (s, 1H), 7.58 (d, J=8.0 Hz, 1H), 7.55-7.46 (m, 1.5H), 7.43-7.34 (m, 2.5H), 7.32-7.25 (m, 1H), 7.07-7.5 (m, 1H), 4.62-4.22 (m, 4H), 3.77 (s, 3H), 3.73 (d, J=17 Hz, 3H), 3.32 (s, 3H).

Workup

  1. customthe reaction
  2. extractionextracted with ethyl acetate
  3. washThe combined extracts were back-washed with water
  4. dry with materialThe resulting organic layer was dried over Na2SO4
  5. filtrationfiltered
  6. customevaporated in vacuo
  7. customto afford a clear oil
  8. customThe resulting oil was purified on SiO2

Sources & evidence

ORD record
ord-40bc7e9682fa41fcb302e1c720a570e2
Source dataset
uspto-grants-2011_05
Patent number
US07935727B2

Reaction notes

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