HCID 178500572, compound → Methyl 3-[3-(3-tert-butyloxycarbonylaminophenyl)-1,2,4-oxadiazol-5-yl]propionate

HRID 584137Notes

Reaction equation

HRID 584137 reaction equation
[C:1]([O:5][C:6]([NH:8][C:9]1[CH:10]=[C:11]([CH:24]=[CH:25][CH:26]=1)[C:12]([NH:14][O:15][C:16](=O)[CH2:17][CH2:18][C:19]([O:21][CH3:22])=[O:20])=[NH:13])=[O:7])([CH3:4])([CH3:3])[CH3:2]>C1(C)C=CC=CC=1>[C:1]([O:5][C:6]([NH:8][C:9]1[CH:10]=[C:11]([C:12]2[N:13]=[C:16]([CH2:17][CH2:18][C:19]([O:21][CH3:22])=[O:20])[O:15][N:14]=2)[CH:24]=[CH:25][CH:26]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

3

Reactant 1

HCID 178500572HCID 178500572, compound

Product 1

HCID 22343240Methyl 3-[3-(3-tert-butyloxycarbonylaminophenyl)-1,2,4-oxadiazol-5-yl]propionate

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A suspension of 3-tert-butyloxycarbonylamino-N-(3-carbomethoxypropionyloxy) benzamidine (8.25 g, 22.6 mmol) in toluene (120 mL) was added to a 250-mL round bottomed flask equipped with a magnetic stirrer and a reflux condenser, and the contents heated to reflux for 5 h. The reaction was then cooled, and the resulting solution concentrated under vacuum. This afforded a quantitative yield of methyl 3-[3-(3-tert-butyloxycarbonylaminophenyl)-1,2,4-oxadiazol-5-yl]propionate as a yellow solid. m.p. 90-91° C.; 1H NMR (CDCl3) δ (ppm) 7.97 (s, 1H), 7.72 (d, 1H,J=7.6 Hz), 7.61 (d, 1H,J=7.6 Hz), 7.39 (m, 2H), 6.57 (bs, 1H), 3.73 (s, 3H), 3.26 (t, 2H,J=7.3 Hz), 2.94 (t, 2H,J=7.3 Hz), 1.53 (s, 9H); m/z=346 (M−H).

Workup

  1. additionwas added to a 250-mL round bottomed flask
  2. customequipped with a magnetic stirrer and a reflux condenser
  3. temperaturethe contents heated
  4. temperatureto reflux for 5 h
  5. temperatureThe reaction was then cooled
  6. concentrationthe resulting solution concentrated under vacuum

Sources & evidence

ORD record
ord-d292a38784274b6591602305febc92f2
Source dataset
uspto-grants-2005_08
Patent number
US06924284B2

Reaction notes

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