Azane;hydrate → Benzyl 2-(7-carbamoylbenzo[d]oxazol-2-yl)pyrrolidine-1-carboxylate

HRID 415250Notes

Reaction equation

HRID 415250 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:15][CH2:14][CH2:13][CH:12]1[C:16]1[O:17][C:18]2[C:24]([C:25](OC)=O)=[CH:23][CH:22]=[CH:21][C:19]=2[N:20]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH2:29].[NH3:30]>CO>[C:25]([C:24]1[C:18]2[O:17][C:16]([CH:12]3[CH2:13][CH2:14][CH2:15][N:11]3[C:9]([O:8][CH2:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)=[O:10])=[N:20][C:19]=2[CH:21]=[CH:22][CH:23]=1)(=[O:29])[NH2:30]

Participants

4

Reactant 2

HCID 12896473Azane;hydrateHCID 66621250Methyl 2-(1-(benzyloxycarbonyl)pyrrolidin-2-yl)benzo[d]oxazole-7-carboxylate

Product 1

HCID 66621188Benzyl 2-(7-carbamoylbenzo[d]oxazol-2-yl)pyrrolidine-1-carboxylateYield 42%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of methyl 2-(1-(benzyloxycarbonyl)pyrrolidin-2-yl)benzo[d]oxazole-7-carboxylate (150 mg, 0.394 mmol) in methanol (8 mL) was added ammonia water (6 mL) at 0° C. After the addition, the mixture was allowed to stir at room temperature overnight. Methanol was removed in vacuum. The residue was diluted with water (100 mL), extracted with ethyl acetate (50 mL×3). The combined organic layers washed with brine, dried over anhydrous sodium sulfate, and concentrated to give crude product. The crude product was purified by chromatography (silica gel, petroleum ether/ethyl acetate=20:1 to 1:1) to give benzyl 2-(7-carbamoylbenzo[d]oxazol-2-yl)pyrrolidine-1-carboxylate (68 mg, yield 42%). LC-MS (ESI) m/z: 366 (M+1)+.

Workup

  1. additionAfter the addition
  2. customMethanol was removed in vacuum
  3. additionThe residue was diluted with water (100 mL)
  4. extractionextracted with ethyl acetate (50 mL×3)
  5. washThe combined organic layers washed with brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated
  8. customto give crude product
  9. customThe crude product was purified by chromatography (silica gel, petroleum ether/ethyl acetate=20:1 to 1:1)

Sources & evidence

ORD record
ord-0c7138c79e374084b98397d109a18bb9
Source dataset
uspto-grants-2012_01
Patent number
US08088760B2

Reaction notes

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