Hydrochloric Acid → Methyl (4R)-4-[(2-ethoxy-7-methoxy-6-vinylquinolin-4-yl)oxy]-L-prolinate dihydrochloride

HRID 1875382Notes

Reaction equation

HRID 1875382 reaction equation
[ClH:1].[CH2:2]([O:4][C:5]1[CH:14]=[C:13]([O:15][C@H:16]2[CH2:20][N:19](C(OC(C)(C)C)=O)[C@H:18]([C:28]([O:30][CH3:31])=[O:29])[CH2:17]2)[C:12]2[C:7](=[CH:8][C:9]([O:34][CH3:35])=[C:10]([CH:32]=[CH2:33])[CH:11]=2)[N:6]=1)[CH3:3]>C(Cl)Cl>[ClH:1].[ClH:1].[CH2:2]([O:4][C:5]1[CH:14]=[C:13]([O:15][C@H:16]2[CH2:20][NH:19][C@H:18]([C:28]([O:30][CH3:31])=[O:29])[CH2:17]2)[C:12]2[C:7](=[CH:8][C:9]([O:34][CH3:35])=[C:10]([CH:32]=[CH2:33])[CH:11]=2)[N:6]=1)[CH3:3]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 580914531-t-Butyl 2-methyl (2S,4R)-4-[(2-ethoxy-7-methoxy-6-vinylquinolin-4-yl)oxy]pyrrolidine-1,2-dicarboxylate

Product 1

HCID 86640851Methyl (4R)-4-[(2-ethoxy-7-methoxy-6-vinylquinolin-4-yl)oxy]-L-prolinate dihydrochloride

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

HCl (g) was bubbled for 10 minutes through a solution of the product from Step 1 (3.90 g, 8.25 mmol) in DCM (83 mL). The solution stirred for 1 hour, and the DCM was removed in vacuo to give 3.55 g of the title compound as a white powder. LRMS ESI+ (M+H−2(HCl))+ 373.1, calcd for C20H25N2O5: 373.2.

Workup

  1. customthe DCM was removed in vacuo

Sources & evidence

ORD record
ord-cc953438ae704a7bae4fbcc8d219c396
Source dataset
uspto-grants-2012_11
Patent number
US08309540B2

Reaction notes

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