Acetic Acid → HCID 59556632, compound

HRID 1172977Notes

Reaction equation

HRID 1172977 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@H:23]4[CH2:25][C@@H:24]4[C:26]([O:28]C)=[O:27])=[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.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@@H:23]4[CH2:25][C@H:24]4[C:26]([OH:28])=[O:27])=[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

6

Reactant 3

HCID 176Acetic AcidHCID 14798Sodium HydroxideHCID 67369637HCID 67369637, compound

Product 1

HCID 59556632HCID 59556632, compoundYield 59.7%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidCatalystHCID 702EthanolSolvent

Procedure

To a suspension of (1S, 2S)-methyl 2-(4-(3-(3-chloro-4-isopropoxyphenyl)-1,2,4-oxadiazol-5-yl)phenyl)cyclopropanecarboxylate (111 mg, 0.269 mmol) in ethanol (5 ml) was added 2 N NaOH (5 ml, 10.00 mmol). The mixture was stirred under nitrogen at room temperature overnight. Reaction mixture was neutralized by addition of acetic acid, and then acidified with a few drops of 1 N aqueous HCl (pH about 2). White solid precipitated and was collected by filtration, washed with 0.1N HCl (3×5 mL), and dried under vacuum to give Trans-2-(4-(3-(3-chloro-4-isopropoxyphenyl)-1,2,4-oxadiazol-5-yl)phenyl)cyclopropanecarboxylic acid (64 mg, 59%). LCMS (Table 1, Method f) Rt=2.99 min, m/z 399.16 (M+H)+. 1H NMR (400 MHz, DMSO) δ ppm 8.07 (d, 2H), 8.05 (d, 1H), 7.99 (dd, 1H), 7.45 (d, 2H), 7.38 (d, 1H), 4.82 (sept., 1H), 2.54 (m, 1H), 1.97 (m, 1H), 1.53 (td, 1H), 1.46 (ddd, 1H), 1.35 (d, 6H).

Workup

  1. customReaction mixture
  2. customWhite solid precipitated
  3. filtrationwas collected by filtration
  4. washwashed with 0.1N HCl (3×5 mL)
  5. customdried under vacuum

Sources & evidence

ORD record
ord-52ef92a739f84ece8dbca8fe6e463541
Source dataset
uspto-grants-2010_11
Patent number
US07834039B2

Reaction notes

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