Hydrochloric Acid → HCID 71238242, compound

HRID 1401881Notes

Reaction equation

HRID 1401881 reaction equation
C([O:5][C:6](=[O:46])[C:7]1[CH:12]=[CH:11][C:10]([C:13](=[O:29])[NH:14][C:15]2[CH:20]=[CH:19][C:18]([C:21]3[CH:26]=[CH:25][C:24](Cl)=[CH:23][C:22]=3[CH3:28])=[CH:17][CH:16]=2)=[CH:9][C:8]=1[CH2:30][CH2:31][C:32]1[CH:37]=[CH:36][CH:35]=[C:34]([C:38]2[CH2:43][CH2:42][C:41]([CH3:45])([CH3:44])[CH2:40][CH:39]=2)[CH:33]=1)(C)(C)C.FC(F)(F)C(O)=O.[ClH:54]>C(Cl)Cl>[Cl:54][C:22]1([CH3:28])[CH2:23][CH:24]=[CH:25][CH:26]=[C:21]1[C:18]1[CH:17]=[CH:16][C:15]([NH:14][C:13]([C:10]2[CH:11]=[CH:12][C:7]([C:6]([OH:46])=[O:5])=[C:8]([CH2:30][CH2:31][C:32]3[CH:37]=[CH:36][CH:35]=[C:34]([C:38]4[CH2:43][CH2:42][C:41]([CH3:45])([CH3:44])[CH2:40][CH:39]=4)[CH:33]=3)[CH:9]=2)=[O:29])=[CH:20][CH:19]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 6422Trifluoroacetic acidHCID 71238500HCID 71238500, compound

Product 1

HCID 71238242HCID 71238242, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 4-{4′-chloro-2′-methyl-biphenyl-4-ylcarbamoyl)-2-[(3-(4,4-dimethyl-cyclohex-1-enyl)-phenyl]-ethyl}-benzoic acid tert-butyl ester (0.82 g, 1.29 mmol) in CH2Cl2 (30 mL) at room temperature, added trifluoroacetic acid (2.5 ml), and conc HCl (1.0 mL) The reaction mixture was stirred overnight. The organic solvents were removed under reduced pressure. The residue was extracted with ethyl acetate (2×100 mL), dried over MgSO4 and concentrated o afford 4-{2′-chloro-2′-methyl-biphenyl-4-ylcarbamoyl)-2-[(3-(4,4-dimethyl-cyclohex-1-enyl)-phenyl]-ethyl}-benzoic acid as a solid. 1H NMR (500 MHz, DMSO-d6): 10.05 (s, 1 H), 7.73 (d, J=8.0 Hz, 2 H), 7.48 (d, J=8.5 Hz, 2 H), 7.40 (s, 1 H), 7.29-7.05 (m, 10 H), 5.99 (s, 1 H), 3.96 (t, J=10.5 Hz. 1 H), 2.95 (dd, J=5.0, 14.0 Hz, 1 H), 2.20-2.18 (m, 1 H), 2.14 (t, J=7.5 Hz, 1 H), 2.09 (s, 3 H), 1.89 (bs, 2 H), 1.49 (t, J=7.5 Hz, 1 H), 1.39 (t, J=6.0 Hz, 2 H), 0.84 (s, 6 H). Chiral HPLC conditions: Chiralcel OD-H T=23° C.; mobile phase=10-30% hexane/IPA; flow rate=1.0 mL/min; detection=254, 280, 220 nm retention time in min: 19.81 min (enantiomeric excess: 70.8%)

Workup

  1. customThe organic solvents were removed under reduced pressure
  2. extractionThe residue was extracted with ethyl acetate (2×100 mL)
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-753c82c823cf43139c0ae52db1dfe00d
Source dataset
uspto-grants-2014_12
Patent number
US08907103B2

Reaction notes

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