Triethylamine → 1-(3-methoxycarbonyl-2-methylpropanoyl)-L-prolineamide

HRID 262756Notes

Reaction equation

HRID 262756 reaction equation
[CH3:1][O:2][C:3]([CH2:5][CH:6]([CH3:17])[C:7]([N:9]1[CH2:16][CH2:15][CH2:14][C@H:10]1[C:11](O)=[O:12])=[O:8])=[O:4].C(OC(Cl)=O)C(C)C.C([N:28](CC)CC)C>ClCCl>[CH3:1][O:2][C:3]([CH2:5][CH:6]([CH3:17])[C:7]([N:9]1[CH2:16][CH2:15][CH2:14][C@H:10]1[C:11]([NH2:28])=[O:12])=[O:8])=[O:4]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 62365Isobutyl chloroformateHCID 538488431-(3-Methoxycarbonyl-2-methylpropanoyl)-L-proline

Product 1

HCID 227996501-(3-methoxycarbonyl-2-methylpropanoyl)-L-prolineamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1-(3-Methoxycarbonyl-2-methylpropanoyl)-L-proline (2.4 g.) is dissolved in a mixture of dichloromethane (50 ml.) and triethylamine (1.4 ml.). The solution is chilled in an ice water bath and isobutylchloroformate (1.36 g.) is added while the mixture is stirred. After 10 minutes ammonia (gas) is bubbled through the solution, still in the ice bath, for fifteen minutes. The reaction mixture is stirred for one hour at room temperature, diluted with methylene chloride (100 ml.) and washed with water, 0.1 N hydrochloric acid, water, and dried over magnesium sulfate. The solvent is removed in vacuo to yield 1-(3-methoxycarbonyl-2-methylpropanoyl)-L-prolineamide.

Workup

  1. temperatureThe solution is chilled in an ice water bath
  2. customAfter 10 minutes ammonia (gas) is bubbled through the solution, still in the ice bath, for fifteen minutes
  3. stirringThe reaction mixture is stirred for one hour at room temperature
  4. additiondiluted with methylene chloride (100 ml.)
  5. washwashed with water, 0.1 N hydrochloric acid, water
  6. dry with materialdried over magnesium sulfate
  7. customThe solvent is removed in vacuo

Sources & evidence

ORD record
ord-de3c76cf5a804ed59f69e0cafeac77cb
Source dataset
uspto-grants-1979_05
Patent number
US04154937

Reaction notes

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