Water → Methyl 2-(1-(benzyloxycarbonyl)pyrrolidin-2-yl)benzo[d]oxazole-7-carboxylate

HRID 415249Notes

Reaction equation

HRID 415249 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[CH2:19][CH2:18][CH2:17][N:16]1[C:20]([O:22][CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)=[O:21])=[O:14].O>P(Cl)(Cl)(Cl)=O>[CH2:23]([O:22][C:20]([N:16]1[CH2:17][CH2:18][CH2:19][CH:15]1[C:13]1[O:14][C:2]2[C:7]([C:8]([O:10][CH3:11])=[O:9])=[CH:6][CH:5]=[CH:4][C:3]=2[N:12]=1)=[O:21])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

4

Reactant 2

HCID 962WaterHCID 66621344Benzyl 2-(2-hydroxy-3-(methoxycarbonyl)phenylcarbamoyl)pyrrolidine-1-carboxylate

Product 1

HCID 66621250Methyl 2-(1-(benzyloxycarbonyl)pyrrolidin-2-yl)benzo[d]oxazole-7-carboxylateYield 45%

Reagents, catalysts & solvents 1

HCID 24813Phosphorus oxychlorideSolvent

Procedure

A mixture of benzyl 2-(2-hydroxy-3-(methoxycarbonyl)phenylcarbamoyl)pyrrolidine-1-carboxylate (400 mg, 1 mmol) in phosphoryl trichloride (5 mL) was heated to reflux for 40 mins. The mixture was cooled to room temperature and poured into water (100 mL) carefully with vigorous stirring, then extracted with ethyl acetate (50 mL×3). The combined organic layers were dried over anhydrous sodium sulfate, and concentrated to give crude product. The crude product was purified by chromatography (silica gel, petroleum ether/ethyl acetate=30:1 to 8:1) to give methyl 2-(1-(benzyloxycarbonyl)pyrrolidin-2-yl)benzo[d]oxazole-7-carboxylate (170 mg, yield 45%). LC-MS (ESI) m/z: 381 (M+1).

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 40 mins
  3. extractionextracted with ethyl acetate (50 mL×3)
  4. dry with materialThe combined organic layers were dried over anhydrous sodium sulfate
  5. concentrationconcentrated
  6. customto give crude product
  7. customThe crude product was purified by chromatography (silica gel, petroleum ether/ethyl acetate=30:1 to 8:1)

Sources & evidence

ORD record
ord-cc4f95da493a4531bf244b722f74dfb6
Source dataset
uspto-grants-2012_01
Patent number
US08088760B2

Reaction notes

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