Diisopropylethylamine → HCID 67100018, compound

HRID 1868894Notes

Reaction equation

HRID 1868894 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([OH:20])=[C:7]([C:15](OCC)=[O:16])[C:8](=[O:14])[C:9]2([CH3:13])[CH3:12])=[CH:4][C:3]=1[F: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:11]=[C:10]2[C:5]([C:6]([OH:20])=[C:7]([C:15]([NH:32][CH2:33][C:34]([O:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[O:35])=[O:16])[C:8](=[O:14])[C:9]2([CH3:13])[CH3:12])=[CH:4][C:3]=1[F:21]

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 2725036Glycine tert-butyl ester hydrochlorideHCID 67099819HCID 67099819, compound

Product 1

HCID 67100018HCID 67100018, compoundYield 19.2%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
80 °C

Procedure

Ethyl 7-chloro-6-fluoro-4-hydroxy-1,1-dimethyl-2-oxo-naphthalene-3-carboxylate (820 mg, 2622 μmol) was dissolved in 1,4-dioxane (5244 μL) and N-ethyl-N-isopropylpropan-2-amine (1370 μL, 7866 μmol). tert-Butyl 2-aminoacetate hydrochloride (659 mg, 3933 μmol) was added, and the reaction was stirred 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 (200 mg) as a white solid after flash chromatography. MS m/e 420 (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-45273019524c4ddfb1a2c5da3bfc3658
Source dataset
uspto-grants-2009_12
Patent number
US07635715B2

Reaction notes

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