Acetic Acid → HCID 25001822, compound

HRID 1172988Notes

Reaction equation

HRID 1172988 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>C(O)C.C(Cl)Cl.Cl.CCOCC>[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 3

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

Product 1

HCID 25001822HCID 25001822, compoundYield 76.5%

Reagents, catalysts & solvents 4

HCID 313Hydrochloric AcidSolventHCID 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 (4mL) and NaOH (4mL, 8.00 mmol) was added. The mixture was stirred at room temperature under nitrogen. After 20 minutes the reaction was neutralized by drop-wise addition of acetic acid. The aqueous mixture was then frozen and lyophilized. The solid obtained after lyophilization was brought up in DCM, filtered, and washed with DCM. The filtrate was concentrated and brought up in ether to provide a slightly cloudy solution. IN HCl in ether was added dropwise until white precipitate formed. 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 f) 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. customThe solid obtained after lyophilization
  3. filtrationfiltered
  4. washwashed with DCM
  5. concentrationThe filtrate was concentrated
  6. customto provide a slightly cloudy solution
  7. customformed
  8. filtrationMaterial was collected by filtration
  9. washwashed with ether
  10. customdried in a vacuum oven

Sources & evidence

ORD record
ord-41e24d38aa4045b3b2889b158c11be84
Source dataset
uspto-grants-2010_11
Patent number
US07834039B2

Reaction notes

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