Trifluoroacetic acid → methyl (2S)-2-amino-3-(quinolin-6-yl)propanoate

HRID 2282912Notes

Reaction equation

HRID 2282912 reaction equation
[CH3:1][O:2][C:3]1[C@H:4]([CH2:14][C:15]2[CH:16]=[C:17]3[C:22](=[CH:23][CH:24]=2)[N:21]=[CH:20][CH:19]=[CH:18]3)[N:5]=C(OC)[C@@H](C(C)C)N=1.FC(F)(F)C(O)=[O:28]>O.C(#N)C>[NH2:5][C@@H:4]([CH2:14][C:15]1[CH:16]=[C:17]2[C:22](=[CH:23][CH:24]=1)[N:21]=[CH:20][CH:19]=[CH:18]2)[C:3]([O:2][CH3:1])=[O:28]

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 866857696-{[(2S,5R)-3,6-dimethoxy-5-(propan-2-yl)-2,5-dihydropyrazin-2-yl]methyl}quinoline

Product 1

HCID 86685770methyl (2S)-2-amino-3-(quinolin-6-yl)propanoate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
10 °C

Procedure

To a solution of #211 (7.3 g, 22.5 mmol, 1 eq.) in water (25 mL) and acetonitrile (80 mL) was added trifluoroacetic acid (9 mL) at 0° C. and the solution was stirred at 10° C. overnight. The organic layer was removed in vacuo and the remaining aqueous layer was basified to pH 9 with sodium carbonate, which was directly used for the next step.

Workup

  1. customThe organic layer was removed in vacuo

Sources & evidence

ORD record
ord-434e164d28574ed5ac9977da72468d43
Source dataset
uspto-grants-2015_09
Patent number
US09138486B2

Reaction notes

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