Hydrochloric Acid → Methyl (4R)-4-[(7-methoxy-2-oxo-6-vinyl-1,2-dihydroquinolin-4-yl)oxy]-L-prolinate hydrochloride

HRID 1423375Notes

Reaction equation

HRID 1423375 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([C:7]([O:14][C@H:15]3[CH2:19][N:18](C(OC(C)(C)C)=O)[C@H:17]([C:27]([O:29][CH3:30])=[O:28])[CH2:16]3)=[CH:8][C:9](=[O:13])[NH:10]2)=[CH:5][C:4]=1[CH:31]=[CH2:32].[ClH:33]>>[ClH:33].[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([C:7]([O:14][C@H:15]3[CH2:19][NH:18][C@H:17]([C:27]([O:29][CH3:30])=[O:28])[CH2:16]3)=[CH:8][C:9](=[O:13])[NH:10]2)=[CH:5][C:4]=1[CH:31]=[CH2:32]

Participants

3

Reactant 2

HCID 313Hydrochloric AcidHCID 592799081-tert-butyl 2-methyl (2S,4R)-4-[(7-methoxy-2-oxo-6-vinyl-1,2-dihydroquinolin-4-yl)oxy]pyrrolidine-1,2-dicarboxylate

Product 1

HCID 86643488Methyl (4R)-4-[(7-methoxy-2-oxo-6-vinyl-1,2-dihydroquinolin-4-yl)oxy]-L-prolinate hydrochloride

Procedure

To the product from Step 3, 1-tert-butyl 2-methyl (2S,4R)-4-[(7-methoxy-2-oxo-6-vinyl-1,2-dihydroquinolin-4-yl)oxy]pyrrolidine-1,2-dicarboxylate (2.02 g, 4.54 mmol) was added HCl (4M in dioxane) (22.72 ml, 91 mmol) at r.t. After 1.5 h, the solvent was removed in vacuo. The residue was taken up in Et2O and the solvent was removed in vacuo to yield 1.73 (99%) g of the title compound as a tan solid. LRMS ESI+ (M+H)+ 345.4.

Workup

  1. customthe solvent was removed in vacuo
  2. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-042f8635dd4549ccb633492c865ba8a6
Source dataset
uspto-grants-2015_01
Patent number
US08927569B2

Reaction notes

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