Sodium Bicarbonate → Methyl 2-(1-(benzyloxycarbonyl)piperidin-3-yl)benzo[d]oxazole-7-carboxylate

HRID 415265Notes

Reaction equation

HRID 415265 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][CH2:14][CH:13]([C:17](=O)[NH:18][C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([C:25]([O:27][CH3:28])=[O:26])[C:20]=2[OH:29])[CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)(O)[O-].[Na+]>C(O)(=O)CC.O>[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][CH2:14][CH:13]([C:17]2[O:29][C:20]3[C:21]([C:25]([O:27][CH3:28])=[O:26])=[CH:22][CH:23]=[CH:24][C:19]=3[N:18]=2)[CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 516892Sodium BicarbonateHCID 66621331Benzyl-3-(2-hydroxy-3-(methoxycarbonyl)phenylcarbamoyl)piperidine-1-carboxylate

Product 1

HCID 66620844Methyl 2-(1-(benzyloxycarbonyl)piperidin-3-yl)benzo[d]oxazole-7-carboxylateYield 91.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1032Propionic AcidSolvent

Procedure

A mixture of benzyl-3-(2-hydroxy-3-(methoxycarbonyl)phenylcarbamoyl)piperidine-1-carboxylate (210 mg, 0.5 mmol) in propionic acid (20 mL) was heated to reflux for 4 days. The mixture was diluted with water (50 mL), neutralized with sodium bicarbonate, and then extracted with ethyl acetate (50 mL×3). The combined organic layers were dried over anhydrous sodium sulfate and concentrated. 180 mg of methyl 2-(1-(benzyloxycarbonyl)piperidin-3-yl)benzo[d]oxazole-7-carboxylate was obtained. Yield: 91%. LC-MS (ESI) m/z: 395 (M+1)+.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 4 days
  3. extractionextracted with ethyl acetate (50 mL×3)
  4. dry with materialThe combined organic layers were dried over anhydrous sodium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-18521769ad3f4e7d953cc35649869429
Source dataset
uspto-grants-2012_01
Patent number
US08088760B2

Reaction notes

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