Diisopropylethylamine → HCID 67099890, compound

HRID 1868790Notes

Reaction equation

HRID 1868790 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:14](=[CH:15][C:16]=1[Cl:17])[C:8]1([CH2:13][CH2:12][O:11][CH2:10][CH2:9]1)[C:7](=[O:18])[C:6]([C:19](OCC)=[O:20])=[C:5]2[OH:24].C(N(C(C)C)C(C)C)C.Cl.[NH2:35][CH2:36][C:37]([O:39][C:40]([CH3:43])([CH3:42])[CH3:41])=[O:38]>O1CCOCC1.CCOC(C)=O>[Cl:1][C:2]1[CH:3]=[C:4]2[C:14](=[CH:15][C:16]=1[Cl:17])[C:8]1([CH2:9][CH2:10][O:11][CH2:12][CH2:13]1)[C:7](=[O:18])[C:6]([C:19]([NH:35][CH2:36][C:37]([O:39][C:40]([CH3:43])([CH3:42])[CH3:41])=[O:38])=[O:20])=[C:5]2[OH:24]

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 2725036Glycine tert-butyl ester hydrochlorideHCID 67099697HCID 67099697, compound

Product 1

HCID 67099890HCID 67099890, compoundYield 51.8%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
80 °C

Procedure

Ethyl 6,7-dichloro-4-hydroxy-2-oxo-2′,3′,5′,6′-tetrahydro-spiro[naphthalene-1,4′-pyran]-3-carboxylate (550 mg, 1482 μmol) was dissolved in 1,4-dioxane (1482 μL), and N-ethyl-N-isopropylpropan-2-amine (774 μL, 4445 μmol). tert-Butyl 2-aminoacetate hydrochloride (373 mg, 2222 μmol) was added to the reaction, and the reaction was stirred at 80° C. for 3 hours. The reaction mixture was 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 (350 mg) as a white solid after flash chromatography. MS (m/z)=456 (M+H)+.

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-281d4e755e324e46905344fa2ca53d03
Source dataset
uspto-grants-2009_12
Patent number
US07635715B2

Reaction notes

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