Methanol → (R)-Methyl 3-hydroxy-2-(5-nitro-1-oxoisoquinolin-2(1H)-yl)propanoate

HRID 1161210Notes

Reaction equation

HRID 1161210 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].CO.C(N(CC)CC)C.Cl.[NH2:25][C@H:26]([CH2:31][OH:32])[C:27]([O:29][CH3:30])=[O:28]>>[OH:32][CH2:31][C@@H:26]([N:25]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:27]([O:29][CH3:30])=[O:28]

Participants

5

Reactant 4

HCID 887MethanolHCID 8471TriethylamineHCID 100127605-nitro-1H-isochromen-1-oneHCID 11446470D-Serine methyl ester hydrochloride

Product 1

HCID 67088204(R)-Methyl 3-hydroxy-2-(5-nitro-1-oxoisoquinolin-2(1H)-yl)propanoate

Conditions

Temperature
70 °C

Procedure

A round bottom flask was charged with 5-nitro-isochromen-1-one (10 g, 0.05 mol), methanol (200 mL, 5 mol), triethylamine (18 mL, 0.13 mol) and (R)-methyl 2-amino-3-hydroxypropanoate hydrochloride (9.8 g, 0.063 mol) where by the reaction became homogeneous. The reaction was then heated at 70° C. overnight. The solvent was removed and the residue purified by flash chromatography (120 g, 0-10% MeOH/DCM) to yield the product as a yellow solid. MS m/z=293.5 (M+H).

Workup

  1. customThe solvent was removed
  2. customthe residue purified by flash chromatography (120 g, 0-10% MeOH/DCM)

Sources & evidence

ORD record
ord-f0b61f54ff8e48d5aaca8cbd1d5df075
Source dataset
uspto-grants-2010_10
Patent number
US07816371B2

Reaction notes

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