Sodium Bicarbonate → HCID 66621319, compound

HRID 415340Notes

Reaction equation

HRID 415340 reaction equation
O[C:2]1[C:7]([C:8]([O:10][CH3:11])=[O:9])=[CH:6][CH:5]=[CH:4][C:3]=1[NH:12][C:13]([CH:15]1[CH2:20][CH2:19][N:18]([C:21]([O:23][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[O:22])[CH2:17][CH2:16]1)=[O:14].C(=O)(O)[O-].[Na+]>C(O)(=O)CC.O>[CH2:24]([O:23][C:21]([N:18]1[CH2:17][CH2:16][CH:15]([C:13]2[O:14][C:2]3[C:7]([C:8]([O:10][CH3:11])=[O:9])=[CH:6][CH:5]=[CH:4][C:3]=3[N:12]=2)[CH2:20][CH2:19]1)=[O:22])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

5

Reactant 2

HCID 516892Sodium BicarbonateHCID 66621303HCID 66621303, compound

Product 1

HCID 66621319HCID 66621319, compoundYield 22.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1032Propionic AcidSolvent

Procedure

A mixture of benzyl 4-(2-hydroxy-3-(methoxycarbonyl)phenylcarbamoyl)piperidine-1-carboxylate (2.63 g, 6.4 mmol) in propionic acid (10 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 washed with brine, dried over anhydrous sodium sulfate, and concentrated to give crude product. The crude product was purified by prep-HPLC to afford methyl 2-(1-(benzyloxycarbonyl)piperidin-4-yl)benzo[d]oxazole-7-carboxylate (560 mg, yield 22%). 1H-NMR (400 MHz, CDCl3) δ (ppm): 1.94-1.98 (m, 2H), 2.20-2.23 (m, 2H), 3.07-3.09 (m, 2H), 3.21-3.24 (m, 1H), 4.00 (s, 3H), 4.23 (brs, 2H), 5.16 (s, 2H), 7.32-7.40 (m, 6H), 7.87-7.89 (dd, J1=7.6 Hz, J2=0.8 Hz, 1H), 7.95-7.97 (dd, J1=8.0 Hz, J2=0.8 Hz, 1H); 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. washThe combined organic layers were washed with brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated
  7. customto give crude product
  8. customThe crude product was purified by prep-HPLC

Sources & evidence

ORD record
ord-d72a49af45694c919bb95b173a5e8035
Source dataset
uspto-grants-2012_01
Patent number
US08088760B2

Reaction notes

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