Acetonitrile → HCID 14555447, compound

HRID 232037Notes

Reaction equation

HRID 232037 reaction equation
[C:1]([O:5][C:6]([NH:8]N[C@H](C(O)=O)C)=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:15](N1C=CN=C1)(N1C=CN=C1)=[O:16].[CH2:27]([N:34]1[CH2:38][CH2:37][CH:36]([NH2:39])[CH2:35]1)[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.[C:40](#N)[CH3:41]>>[CH3:4][C:1]([O:5][C:6](=[O:7])[NH:8][CH:40]([CH3:41])[C:15](=[O:16])[NH:39][CH:36]1[CH2:37][CH2:38][N:34]([CH2:27][C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=2)[CH2:35]1)([CH3:2])[CH3:3]

Participants

5

Reactant 4

HCID 6342AcetonitrileHCID 682631,1'-CarbonyldiimidazoleHCID 27566131-Benzyl-3-aminopyrrolidineHCID 54249490HCID 54249490, compound

Product 1

HCID 14555447HCID 14555447, compound

Procedure

To a solution of 9.46 g (50 mmol) of t-butoxycarbonylamino-L-alanine (Sigma) in 100 ml of acetonitrile was added 8.1 g (50 mmol) of 1,1'-carbonyldiimidazole. After gas evolution ceased, the reaction mixture was heated at 60° for one hour and allowed to stand at room temperature for 18 hours. The reaction was cooled to 0° and treated with 8.8 g (150 mmole) of 1-benzyl-3-pyrrolidinamine (J. Med. Chem., 24, 1229 (1981)). The reaction was stirred at room temperature for three hours and the solvent was removed in vacuo. The residue was dissolved in ethyl acetate, washed with water, dried (MgSO4) and evaporated in vacuo to give 16.1 g of the title compound with crystallized on standing and had, mp 83°-85°.

Workup

  1. temperaturethe reaction mixture was heated at 60° for one hour
  2. temperatureThe reaction was cooled to 0°
  3. customthe solvent was removed in vacuo
  4. dissolutionThe residue was dissolved in ethyl acetate
  5. washwashed with water
  6. dry with materialdried (MgSO4)
  7. customevaporated in vacuo

Sources & evidence

ORD record
ord-2795f0555b954b30a338af0779e4e9c3
Source dataset
uspto-grants-1989_07
Patent number
US04851418

Reaction notes

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