Diisopropylethylamine → HCID 67100099, compound

HRID 1868780Notes

Reaction equation

HRID 1868780 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[F:12])[C:8]([CH3:14])([CH3:13])[C:7](=[O:15])[C:6]([C:16](OCC)=[O:17])=[C:5]2[OH:21].C(N(C(C)C)C(C)C)C.Cl.[NH2:32][CH2:33][C:34]([O:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[O:35]>O1CCOCC1.CCOC(C)=O>[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[F:12])[C:8]([CH3:13])([CH3:14])[C:7](=[O:15])[C:6]([C:16]([NH:32][CH2:33][C:34]([O:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[O:35])=[O:17])=[C:5]2[OH:21]

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 2725036Glycine tert-butyl ester hydrochlorideHCID 67099551HCID 67099551, compound

Product 1

HCID 67100099HCID 67100099, compoundYield 42.5%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
80 °C

Procedure

To a mixture of ethyl 6,7-difluoro-4-hydroxy-1,1-dimethyl-2-oxo-naphthalene-3-carboxylate (570 mg, 1924 μmol) in 1,4-dioxane (3848 μL) and N-ethyl-N-isopropylpropan-2-amine (1005 μL, 5772 μmol), was added tert-butyl 2-aminoacetate hydrochloride (484 mg, 2886 μmol). The reaction was then heated at 80° C. for 3 hours. The reaction mixture was then diluted with 100 mL of EtOAc, added to a separatory funnel, partitioned with NaHCO3 (saturated, aqueous), washed 2 times with 50 mL of NaHCO3 (saturated, aqueous), separated, dried over Na2SO4, and concentrated in vacuo to give the title compound (312 mg) as a white solid after flash chromatography. MS (m/z)=404(M+Na)+.

Workup

  1. additionadded to a separatory funnel
  2. custompartitioned with NaHCO3 (saturated, aqueous)
  3. washwashed 2 times with 50 mL of NaHCO3 (saturated, aqueous)
  4. customseparated
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-43a781982e5f473b839f5e640aefcc94
Source dataset
uspto-grants-2009_12
Patent number
US07635715B2

Reaction notes

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