Triethylamine → cbz-l-prolinamide

HRID 620918Notes

Reaction equation

HRID 620918 reaction equation
[C:1]([N:11]1[CH2:15][CH2:14][CH2:13][C@H:12]1[C:16]([OH:18])=O)([O:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:2].C([N:21](CC)CC)C.ClC(OCC(C)C)=O>C(Cl)(Cl)Cl>[C:1]([N:11]1[CH2:15][CH2:14][CH2:13][C@H:12]1[C:16]([NH2:21])=[O:18])([O:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:2]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 62365Isobutyl chloroformateHCID 101987Benzyloxycarbonyl-L-proline

Product 1

HCID 6950961cbz-l-prolinamideYield 88%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of the resulting (S)-1-carbobenzoxypyrrolidine-2-carboxylic acid (52.2 g:0.21 mole) and triethylamine (21.2 g:0.21 mole) in 525 ml of chloroform was added isobutyl chloroformate (28.7 g:0.21 mole) with stirring under cooling on ice, followed by continuing the stirring for 15 minutes. Dried ammonia gas was bubbled into the mixture for 1 hour and then the mixture was allowed to warm to room temperature and stand overnight. The resulting white precipitate was removed by the filtration, and the filtrate was evaporated under reduced pressure. The residue was dissolved in 200 ml of chloroform and was washed with diluted aqueous hydrochloric acid and water, and dried over magnesium sulfate. Chloroform was distilled off to give 45.8 g of (S)-1-carbobenzoxypyrrolidine-2-carboxamide. Yield: 88%.

Workup

  1. temperatureunder cooling on ice
  2. customstirring for 15 minutes
  3. customDried ammonia gas was bubbled into the mixture for 1 hour
  4. customThe resulting white precipitate was removed by the filtration
  5. customthe filtrate was evaporated under reduced pressure
  6. dissolutionThe residue was dissolved in 200 ml of chloroform
  7. washwas washed with diluted aqueous hydrochloric acid and water
  8. dry with materialdried over magnesium sulfate
  9. distillationChloroform was distilled off

Sources & evidence

ORD record
ord-fee1db1801e84a39bd7937c5359ed4fc
Source dataset
uspto-grants-1989_04
Patent number
US04822892

Reaction notes

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