Hydrochloric Acid → 3-{4-[6-(4-tert-butylphenylcarbamoyl)-1H-indol-2-yl]-3,5-dimethylphenyl}-propionic acid

HRID 1514960Notes

Reaction equation

HRID 1514960 reaction equation
C[O:2][C:3](=[O:36])[CH2:4][CH2:5][C:6]1[CH:11]=[C:10]([CH3:12])[C:9]([C:13]2[NH:14][C:15]3[C:20]([CH:21]=2)=[CH:19][CH:18]=[C:17]([C:22](=[O:34])[NH:23][C:24]2[CH:29]=[CH:28][C:27]([C:30]([CH3:33])([CH3:32])[CH3:31])=[CH:26][CH:25]=2)[CH:16]=3)=[C:8]([CH3:35])[CH:7]=1.[OH-].[Na+].Cl>C1COCC1.CCOCC>[C:30]([C:27]1[CH:28]=[CH:29][C:24]([NH:23][C:22]([C:17]2[CH:16]=[C:15]3[C:20]([CH:21]=[C:13]([C:9]4[C:8]([CH3:35])=[CH:7][C:6]([CH2:5][CH2:4][C:3]([OH:36])=[O:2])=[CH:11][C:10]=4[CH3:12])[NH:14]3)=[CH:19][CH:18]=2)=[O:34])=[CH:25][CH:26]=1)([CH3:33])([CH3:32])[CH3:31]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 669660003-{4-[6-(4-tert-butylphenylcarbamoyl)-1H-indol-2-yl]-3,5-dimethylphenyl}-propionic acid methyl ester

Product 1

HCID 669651463-{4-[6-(4-tert-butylphenylcarbamoyl)-1H-indol-2-yl]-3,5-dimethylphenyl}-propionic acid

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 3-{4-[6-(4-tert-butylphenylcarbamoyl)-1H-indol-2-yl]-3,5-dimethylphenyl}-propionic acid methyl ester and 1N NaOH (500 μL) in THF (5 mL) was heated at 50° C. for 18 h. The mixture was cooled and was neutralized with one equivalent of 1N HCl and partitioned between water and ethyl acetate. The ethyl acetate layer was dried, filtered, and the solvent removed under reduced pressure to leave an oil, which was twice taken up in ether and solvent removed under reduced pressure to give 3-{4-[6-(4-tert-butylphenylcarbamoyl)-1H-indol-2-yl]-3,5-dimethylphenyl}-propionic acid. 1H NMR (Acetonitrile-d3, 400 MHz): δ 9.62 (s, 1H), 8.72 (s, 1H), 8.04 (s, 1H), 7.63 (m, 4H), 7.40 (d, J=8.7 Hz, 2H), 7.03 (s, 2H), 6.40 (s, 1H), 2.87 (t, J=7.6 Hz, 2H), 2.63 (t, J=7.7 Hz, 2H), 2.11 (s, 6H), 1.32 (s, 9H). MS (m/z) 469.3 (M+1); Retention time=1.50 min (Method 10).

Workup

  1. temperatureThe mixture was cooled
  2. custompartitioned between water and ethyl acetate
  3. dry with materialThe ethyl acetate layer was dried
  4. filtrationfiltered
  5. customthe solvent removed under reduced pressure
  6. customto leave an oil, which
  7. customsolvent removed under reduced pressure

Sources & evidence

ORD record
ord-dd56a719c06d43be86fe6c24b8bed073
Source dataset
uspto-grants-2012_07
Patent number
US08222248B2

Reaction notes

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