Diisopropylethylamine → HCID 67099736, compound

HRID 1868907Notes

Reaction equation

HRID 1868907 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8]([CH3:13])([CH3:12])[C:7](=[O:14])[C:6]([C:15](OCC)=[O:16])=[C:5]2[OH:20].Cl.[CH3:22][O:23][C:24](=[O:28])[C@@H:25]([CH3:27])[NH2:26].C(N(C(C)C)C(C)C)C>O1CCOCC1>[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8]([CH3:12])([CH3:13])[C:7](=[O:14])[C:6]([C:15]([NH:26][C@@H:25]([C:24]([O:23][CH3:22])=[O:28])[CH3:27])=[O:16])=[C:5]2[OH:20]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 11182647Methyl D-alaninate hydrochlorideHCID 67099655HCID 67099655, compound

Product 1

HCID 67099736HCID 67099736, compoundYield 65.4%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
80 °C

Procedure

To ethyl 6-chloro-4-hydroxy-1,1-dimethyl-2-oxo-naphthalene-3-carboxylate (100 mg, 339 μmol, see Example 2) and D-alanine methyl ester hydrochloride (71 mg, 509 mmol) was added 1,4-dioxane (339 μL) and N-ethyl-N-isopropylpropan-2-amine (177 μL, 1018 μmol). The reaction was then heated at 80° C. for 16 hours. The resulting reaction mixture was evaporated to give the title compound (78 mg) as an amorphous solid after purification via preparatory LC. MS m/e=352 (M+1)+.

Workup

  1. customThe resulting reaction mixture
  2. customwas evaporated

Sources & evidence

ORD record
ord-d02607be85b9441caf28d6a8f6b49ea9
Source dataset
uspto-grants-2009_12
Patent number
US07635715B2

Reaction notes

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