Methanol → (R)-Methyl 3-methyl-2-(5-nitro-1-oxoisoquinolin-2(1H)-yl)butanoate

HRID 1161240Notes

Reaction equation

HRID 1161240 reaction equation
[N+:1]([C:4]1[CH:13]=[CH:12][CH:11]=[C:10]2[C:5]=1[CH:6]=[CH:7]O[C:9]2=[O:14])([O-:3])=[O:2].Cl.[CH3:16][O:17][C:18](=[O:24])[C@@H:19]([CH:21]([CH3:23])[CH3:22])[NH2:20].CO.C(N(CC)CC)C>>[CH3:22][CH:21]([CH3:23])[C@@H:19]([N:20]1[CH:7]=[CH:6][C:5]2[C:10](=[CH:11][CH:12]=[CH:13][C:4]=2[N+:1]([O-:3])=[O:2])[C:9]1=[O:14])[C:18]([O:17][CH3:16])=[O:24]

Participants

5

Reactant 4

HCID 887MethanolHCID 8471TriethylamineHCID 100127605-nitro-1H-isochromen-1-oneHCID 11984198Methyl D-valinate hydrochloride

Product 1

HCID 59515729(R)-Methyl 3-methyl-2-(5-nitro-1-oxoisoquinolin-2(1H)-yl)butanoate

Procedure

5-nitro-isochromen-1-one (5 g, 0.03 mol) and D-Valine methyl ester hydrochloride (5 g, 0.03 mol) were refluxed in methanol (40 mL, 1 mol) with triethylamine (5 g, 0.05 mol) for 2 hours. The volatiles were removed via rotovapor, and the residue was purified via flash column chromatography (40 g of silica gel, 0-30% EtOAc/Hexane) to yield a brown oil. MS m/z 305.2 (M+H)+.

Workup

  1. customThe volatiles were removed via rotovapor
  2. customthe residue was purified via flash column chromatography (40 g of silica gel, 0-30% EtOAc/Hexane)
  3. customto yield a brown oil

Sources & evidence

ORD record
ord-194bd61f26924ce2878912a8ae771460
Source dataset
uspto-grants-2010_10
Patent number
US07816371B2

Reaction notes

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