Ammonium Chloride → trans-2-({4'-[(5-Methyl-1,3-benzoxazol-2-yl)amino]biphenyl-4-yl}carbonyl)cyclohexanecarboxylic acid

HRID 9620Notes

Reaction equation

HRID 9620 reaction equation
C[Si](C)(C)CC[O:5][C:6]([C@@H:8]1[CH2:13][CH2:12][CH2:11][CH2:10][C@H:9]1[C:14]([C:16]1[CH:21]=[CH:20][C:19]([C:22]2[CH:27]=[CH:26][C:25]([NH:28][C:29]3[O:30][C:31]4[CH:37]=[CH:36][C:35]([CH3:38])=[CH:34][C:32]=4[N:33]=3)=[CH:24][CH:23]=2)=[CH:18][CH:17]=1)=[O:15])=[O:7].[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[NH4+].[Cl-]>C1COCC1.CCOC(C)=O.O>[CH3:38][C:35]1[CH:36]=[CH:37][C:31]2[O:30][C:29]([NH:28][C:25]3[CH:26]=[CH:27][C:22]([C:19]4[CH:20]=[CH:21][C:16]([C:14]([C@@H:9]5[CH2:10][CH2:11][CH2:12][CH2:13][C@H:8]5[C:6]([OH:7])=[O:5])=[O:15])=[CH:17][CH:18]=4)=[CH:23][CH:24]=3)=[N:33][C:32]=2[CH:34]=1

Participants

7

Reactant 3

HCID 25517Ammonium ChlorideHCID 2724141Tetrabutylammonium FluorideHCID 58681282trans-2-(Trimethylsilyl)ethyl-2-({4'-[(5-methyl-1,3-benzoxazol-2-yl)amino]biphenyl-4-yl}carbonyl)cyclohexanecarboxylate

Product 1

HCID 58681286trans-2-({4'-[(5-Methyl-1,3-benzoxazol-2-yl)amino]biphenyl-4-yl}carbonyl)cyclohexanecarboxylic acidYield 84%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of trans-2-(trimethylsilyl)ethyl-2-({4′-[(5-methyl-1,3-benzoxazol-2-yl)-amino]biphenyl-4-yl}carbonyl)cyclohexanecarboxylate (64 mg, 0.12mmol) in THF (2 mL) was added tetrabutylammonium fluoride (1.0 M in THF, 0.70 mL), and then the reaction mixture was stirred at rt for 16 h. Saturated aqueous NH4Cl was added, and the reaction mixture was diluted with EtOAc and water. The organic layer was separated and the aqueous layer was extracted with EtOAc. The combined organic phases were washed with water and brine, dried over Na2SO4, filtered, and evaporated under reduced pressure. The residue was treated with MeOH, and the precipitate was collected by filtration and dried in a vacuum oven to give trans-2-({4′-[(5-methyl-1,3-benzoxazol-2-yl)amino]biphenyl-4-yl}carbonyl)cyclohexanecarboxylic acid (44.3 mg, 84%). LC-MS m/z 455.3 (MH+), ret. time 3.57 min. 1H NMR (400 MHz, DMSO-d6) δ 1.21 (m, 1H), 1.37 (m, 2H), 1.63 (m, 1H), 1.85 (m, 3H), 2.05 (m, 1H), 2.38 (s, 3H), 2.69 (m, 1H), 3.95 (m, 1H), 7.03 (d, 1H), 7.33 (d, 2H), 7.76 (m, 4H), 7.85 (d, 2H), 7.93 (d, 2H), 10.73 (s, 1H).

Workup

  1. customThe organic layer was separated
  2. extractionthe aqueous layer was extracted with EtOAc
  3. washThe combined organic phases were washed with water and brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. customevaporated under reduced pressure
  7. additionThe residue was treated with MeOH
  8. filtrationthe precipitate was collected by filtration
  9. customdried in a vacuum oven

Sources & evidence

ORD record
ord-8712231646084d08be809f790c04ef32
Source dataset
uspto-grants-2006_08
Patent number
US07091228B2

Reaction notes

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