Methyl L-prolinate → HCID 11500118, compound

HRID 916345Notes

Reaction equation

HRID 916345 reaction equation
[C:1]([C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6](F)=[CH:5][CH:4]=1)#[N:2].[CH3:14][O:15][C:16](=[O:22])[C@@H:17]1[CH2:21][CH2:20][CH2:19][NH:18]1>>[CH3:14][O:15][C:16]([C@@H:17]1[CH2:21][CH2:20][CH2:19][N:18]1[C:6]1[C:7]2[C:12](=[CH:11][CH:10]=[CH:9][CH:8]=2)[C:3]([C:1]#[N:2])=[CH:4][CH:5]=1)=[O:22]

Participants

3

Reactant 2

HCID 853477Methyl L-prolinateHCID 27367341-Cyano-4-fluoronaphthalene

Product 1

HCID 11500118HCID 11500118, compoundYield 1.7%

Procedure

1-Cyano-4-fluoronaphthalene (109 mg, 0.64 mmol) and L-proline methyl ester (380 mg, 2.95 mmol) were heated to 60° C. for 2 days in a sealed vial. The crude product was concentrated in vacuo and purified by preparative TLC (ethyl acetate/n-heptane 1:3, 3× eluted) to afford the title compound (2.9 mg, 1.7%) as an off-white solid.

Workup

  1. concentrationThe crude product was concentrated in vacuo
  2. custompurified by preparative TLC (ethyl acetate/n-heptane 1:3, 3× eluted)

Sources & evidence

ORD record
ord-be84f5dc505549149861a20c4a65038f
Source dataset
uspto-grants-2007_09
Patent number
US07268232B2

Reaction notes

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