Methanol → 3-[3-(3-Tert-butyloxycarbonylaminophenyl)-1,2,4-oxadiazol-5-yl]propionic acid

HRID 584140Notes

Reaction equation

HRID 584140 reaction equation
[C:1]([O:5][C:6]([NH:8][C:9]1[CH:10]=[C:11]([C:15]2[N:19]=[C:18]([CH2:20][CH2:21][C:22]([O:24]C)=[O:23])[O:17][N:16]=2)[CH:12]=[CH:13][CH:14]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH-].[Li+].CO.O>C1COCC1>[C:1]([O:5][C:6]([NH:8][C:9]1[CH:10]=[C:11]([C:15]2[N:19]=[C:18]([CH2:20][CH2:21][C:22]([OH:24])=[O:23])[O:17][N:16]=2)[CH:12]=[CH:13][CH:14]=1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 887MethanolHCID 962WaterHCID 3939Lithium HydroxideHCID 22343240Methyl 3-[3-(3-tert-butyloxycarbonylaminophenyl)-1,2,4-oxadiazol-5-yl]propionate

Product 1

HCID 223431013-[3-(3-Tert-butyloxycarbonylaminophenyl)-1,2,4-oxadiazol-5-yl]propionic acidYield 83%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A 100-mL round bottomed flask was charged with methyl 3-[3-(3-tert-butyloxycarbonylaminophenyl)-1,2,4-oxadiazol-5-yl]propionate (4.04 g, 11.6 mmol), lithium hydroxide (1.39 g, 58.2 mmol), methanol (15 mL), water (15 mL) and THF (15 mL). The resulting solution was then stirred for 2 h at room temperature. The solvents were then removed under reduced pressure and the residue dissolved into water (60 mL). The resulting solution was cooled to 0° C. and acidified to pH 5 by the addition of 2 N hydrochloric acid. The mixture was then extracted with ethyl acetate (4×50 mL) and the combined extracts dried over sodium sulfate. Filtration and concentration under reduced pressure afforded an 83% yield of 3-[3-(3-tert-butyloxycarbonylaminophenyl)-1,2,4-oxadiazol-5-yl]propionic acid as a white solid. m.p. 143-144° C.; 1H NMR (DMSO-d6) δ (ppm) 12.42 (bs, 1H), 9.60 (s, 1H), 8.24 (s, 1H), 7.57 (m, 2H), 7.42 (t, 1H,J=7.9 Hz), 3.26 (t, 2H,J=6.9 Hz), 2.84 (t, 2H,J=6.9 Hz), 1.49 (s, 9H); m/z=332 (M−H).

Workup

  1. customThe solvents were then removed under reduced pressure
  2. dissolutionthe residue dissolved into water (60 mL)
  3. temperatureThe resulting solution was cooled to 0° C.
  4. additionacidified to pH 5 by the addition of 2 N hydrochloric acid
  5. extractionThe mixture was then extracted with ethyl acetate (4×50 mL)
  6. dry with materialthe combined extracts dried over sodium sulfate
  7. filtrationFiltration and concentration under reduced pressure

Sources & evidence

ORD record
ord-7dc05385d4c549908ef2ecb5877a4b34
Source dataset
uspto-grants-2005_08
Patent number
US06924284B2

Reaction notes

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