1,1'-Carbonyldiimidazole → 1-[3-(2-quinolylcarbonyl)propionyl]-L-proline

HRID 66542Notes

Reaction equation

HRID 66542 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[C:11]([CH2:13][CH2:14][C:15]([OH:17])=O)=[O:12].[NH:18]1[CH2:25][CH2:24][CH2:23][C@H:19]1[C:20]([OH:22])=[O:21].C(N1C=CN=C1)(N1C=CN=C1)=O>O1CCCC1>[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[C:11]([CH2:13][CH2:14][C:15]([N:18]1[CH2:25][CH2:24][CH2:23][C@H:19]1[C:20]([OH:22])=[O:21])=[O:17])=[O:12]

Participants

5

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 145742L-ProlineHCID 205300133-(2-Quinolylcarbonyl)propionic acid

Product 1

HCID 537775761-[3-(2-quinolylcarbonyl)propionyl]-L-proline

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

As for Example 6, 3-(2-quinolylcarbonyl)propionic acid (0.01 mole) is coupled to L-proline (0.011 mole) with 1,1'-carbonyldiimidazole (0.01 mole) in tetrahydrofuran to give 1-[3-(2-quinolylcarbonyl)propionyl]-L-proline. Bromination of the preceding compound and reaction of the resulting compound with sodium thioacetate gives the product of the Example.

Sources & evidence

ORD record
ord-eb91fea4b1b04729a1c5b4bc92f97a57
Source dataset
uspto-grants-1982_08
Patent number
US04342691

Reaction notes

Loading…