Triethylamine → N-cyanoacetyl-L-alanyl-L-proline anilide

HRID 1448732Notes

Reaction equation

Br.[NH2:2][C@H:3]([C:5]([N:7]1[CH2:20][CH2:19][CH2:18][C@H:8]1[C:9]([NH:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:10])=[O:6])[CH3:4].[C:21]([CH2:23][C:24](O)=[O:25])#[N:22].C(N(CC)CC)C>ClCCl>[C:21]([CH2:23][C:24]([NH:2][C@H:3]([C:5]([N:7]1[CH2:20][CH2:19][CH2:18][C@H:8]1[C:9]([NH:11][C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1)=[O:10])=[O:6])[CH3:4])=[O:25])#[N:22]

Participants

Conditions

Temperature: 0 °C

Procedure

1.7 g (0.005 mol) of L-alanyl-L-proline anilide hydrobromide were dissolved in 50 ml of dichloromethane at 0° C. 0.42 g (0.005 mol) of cyanoacetic acid, 0.7 ml (0.005 mol) of triethylamine and 1.1 g of N,N-dicyclohexylcarbodiimide were added and the mixture was stirred at 0° C. overnight. The solvent was removed by evaporation, the residue suspended in 50 ml of ethyl acetate, the suspension filtered and the filtrate washed with 1-N hydrochloric acid, water, 5% sodium bicarbonate solution and water, dried over magnesium sulphate and evaporated to give a white solid. Recrystallisation of this solid from ethyl acetate yielded 0.6 g (37%) of N-cyanoacetyl-L-alanyl-L-proline anilide of melting point 183°-184° C.; [α]D20 =-204.6° (c=0.78% in methanol).

Workup

customThe solvent was removed by evaporation
filtrationthe suspension filtered
washthe filtrate washed with 1-N hydrochloric acid, water, 5% sodium bicarbonate solution and water
dry with materialdried over magnesium sulphate
customevaporated
customto give a white solid
customRecrystallisation of this solid from ethyl acetate

Sources & evidence

ORD record: ord-507b0ac3163f4528ae6d71e4d2e3027e
Source dataset: uspto-grants-1980_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04187216

Reaction notes

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