Acetic Acid → HCID 25001822, compound

HRID 1172932Notes

Reaction equation

HRID 1172932 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:12]2[N:16]=[C:15]([C:17]3[CH:22]=[CH:21][C:20]([C:23]([NH:26][CH2:27][CH2:28][C:29]([O:31]C)=[O:30])([CH3:25])[CH3:24])=[CH:19][CH:18]=3)[O:14][N:13]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH:9]([CH3:11])[CH3:10].[OH-].[Na+].C(O)(=O)C.Cl>C(O)C.CCOCC.C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[C:4]([C:12]2[N:16]=[C:15]([C:17]3[CH:22]=[CH:21][C:20]([C:23]([NH:26][CH2:27][CH2:28][C:29]([OH:31])=[O:30])([CH3:25])[CH3:24])=[CH:19][CH:18]=3)[O:14][N:13]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH:9]([CH3:11])[CH3:10]

Participants

8

Reactant 4

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 53247540HCID 53247540, compound

Product 1

HCID 25001822HCID 25001822, compoundYield 76.5%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

Methyl 3-(2-(4-(3-(3-chloro-4-isopropoxyphenyl)-1,2,4-oxadiazol-5-yl)phenyl)propan-2-ylamino)propanoate (83 mg, 0.181 mmol) was dissolved in ethanol (4 mL) and NaOH (4 mL, 8.00 mmol) was added. The mixture was stirred at room temperature under nitrogen. After about 20 minutes the reaction was neutralized by drop-wise addition of acetic acid. The aqueous mixture was then frozen and lyophilized. DCM was added to the solid, filtered, and washed with DCM. The filtrate was concentrated and ether added to afford a slightly cloudy solution. 1N HCl in ether was added dropwise until white precipitate formed. The material was collected by filtration, washed with ether, and dried in a vacuum oven to give 3-(2-(4-(3-(3-chloro-4-isopropoxyphenyl)-1,2,4-oxadiazol-5-yl)phenyl)propan-2-ylamino)propanoic acid as the hydrochloric acid salt (61.5 mg; 70.6%). LCMS (Table 1, Method a) Rt=1.98 min, m/z =444.29 (M+H)+; 1H NMR (400 MHz, DMSO-d6) δ ppm 8.32 (d, J=8.57 Hz, 2H), 8.12 (d, J=2.08 Hz, 1H), 8.03 (dd, J=8.64, 2.10 Hz, 1H), 7.85 (d, J=8.59 Hz, 2H), 7.25 (d, J=8.78 Hz, 1H), 4.79 (sept, J=6.11 Hz, 1H), 2.95 (t, J=6.20 Hz, 2H), 2.44 (t, J=6.17 Hz, 2H), 1.84 (s, 6H), 1.40 (d, J=6.04 Hz, 6H).

Workup

  1. temperatureThe aqueous mixture was then frozen
  2. filtrationfiltered
  3. washwashed with DCM
  4. concentrationThe filtrate was concentrated
  5. additionether added
  6. customto afford a slightly cloudy solution
  7. customformed
  8. filtrationThe material was collected by filtration
  9. washwashed with ether
  10. customdried in a vacuum oven

Sources & evidence

ORD record
ord-63f2fc133ad64486bb504c01130d53df
Source dataset
uspto-grants-2010_11
Patent number
US07834039B2

Reaction notes

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