Hydrochloric Acid → Methyl (4R)-4-[(7-methoxy-3-vinylquinolin-2-yl)oxy]-L-prolinate hydrochloride

HRID 389213Notes

Reaction equation

HRID 389213 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([CH:7]=[C:8]([CH:30]=[CH2:31])[C:9]([O:13][C@H:14]3[CH2:18][N:17](C(OC(C)(C)C)=O)[C@H:16]([C:26]([O:28][CH3:29])=[O:27])[CH2:15]3)=[N:10]2)=[CH:5][CH:4]=1.[ClH:32]>O1CCOCC1>[ClH:32].[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([CH:7]=[C:8]([CH:30]=[CH2:31])[C:9]([O:13][C@H:14]3[CH2:18][NH:17][C@H:16]([C:26]([O:28][CH3:29])=[O:27])[CH2:15]3)=[N:10]2)=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 592872741-t-Butyl 2-methyl (2S,4R)-4-[(7-methoxy-3-vinylquinolin-2-yl)oxy]pyrrolidine-1,2-dicarboxylate

Product 1

HCID 66895950Methyl (4R)-4-[(7-methoxy-3-vinylquinolin-2-yl)oxy]-L-prolinate hydrochloride

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A solution of 1-t-butyl 2-methyl (2S,4R)-4-[(7-methoxy-3-vinylquinolin-2-yl)oxy]pyrrolidine-1,2-dicarboxylate (0.85 g, 1.98 mmol) in 4M HCl in dioxane (10 mL) was stirred at RT for two hours. The reaction mixture was concentrated, and the product was used with no further purification. LRMS (M+H-tBu)+=329.3.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customthe product was used with no further purification

Sources & evidence

ORD record
ord-d16c663562324c14959f82a69853d708
Source dataset
uspto-grants-2013_02
Patent number
US08377874B2

Reaction notes

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