Diisopropylethylamine → HCID 67100102, compound

HRID 1868772Notes

Reaction equation

HRID 1868772 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([F:12])[CH:11]=1)[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>[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([F:12])[CH:11]=1)[C:8]([CH3:14])([CH3:13])[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 67099749HCID 67099749, compound

Product 1

HCID 67100102HCID 67100102, compoundYield 23.8%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
80 °C

Procedure

Ethyl 6-chloro-8-fluoro-4-hydroxy-1,1-dimethyl-2-oxo-naphthalene-3-carboxylate (0.75 g, 2398 μmol) was dissolved in 1,4-dioxane (4797 μL) and N-ethyl-N-isopropylpropan-2-amine (1253 μL, 7195 μmol). tert-Butyl 2-aminoacetate hydrochloride (603 mg, 3597 μmol) was added, and the reaction was stirred at 80° C. for 3 hours. The reaction was then diluted with 150 mL of EtOAc, added to a separatory funnel, partitioned with NaHCO3 (saturated, aqueous), washed 2 times with 75 mL of NaHCO3 (saturated, aqueous), separated, dried over Na2SO4, and concentrated in vacuo to give the title compound (227 mg) as a white solid. MS (m/z)=420(M+Na)+.

Workup

  1. additionadded to a separatory funnel
  2. custompartitioned with NaHCO3 (saturated, aqueous)
  3. washwashed 2 times with 75 mL of NaHCO3 (saturated, aqueous)
  4. customseparated
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-6d821f81f5ad45d3a1e19383eedb26c6
Source dataset
uspto-grants-2009_12
Patent number
US07635715B2

Reaction notes

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