Diisopropylethylamine → HCID 67099828, compound

HRID 1868887Notes

Reaction equation

HRID 1868887 reaction equation
[OH:1][C:2]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:5]2([CH2:10][CH2:9][O:8][CH2:7][CH2:6]2)[C:4](=[O:17])[C:3]=1[C:18](OCC)=[O:19].C(N(C(C)C)C(C)C)C.Cl.[NH2:33][CH2:34][C:35]([O:37][C:38]([CH3:41])([CH3:40])[CH3:39])=[O:36]>O1CCOCC1.CCOC(C)=O>[OH:1][C:2]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:5]2([CH2:10][CH2:9][O:8][CH2:7][CH2:6]2)[C:4](=[O:17])[C:3]=1[C:18]([NH:33][CH2:34][C:35]([O:37][C:38]([CH3:41])([CH3:40])[CH3:39])=[O:36])=[O:19]

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 2725036Glycine tert-butyl ester hydrochlorideHCID 67099917HCID 67099917, compound

Product 1

HCID 67099828HCID 67099828, compoundYield 46.8%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
80 °C

Procedure

Ethyl 4-hydroxy-2-oxo-2′,3′,5′,6′-tetrahydro-spiro[naphthalene-1,4′-pyran]-3-carboxylate (450 mg, 1488 μmol) was dissolved in 1,4-dioxane (1488 μL) and N-ethyl-N-isopropylpropan-2-amine (778 mL, 4465 μmol). tert-Butyl 2-aminoacetate hydrochloride (374 mg, 2233 μmol) was added, and the mixture was heated at 80° C. for 3 hours. The resulting mixture was then cooled to ambient temperature, diluted with 100 mL of EtOAc, added to a separatory funnel, partitioned with NaHCO3 (saturated, aqueous), washed with NaHCO3 (saturated, aqueous) (2×75 mL), separated, dried over Na2SO4, and concentrated in vacuo to give the title compound (270 mg) as a white solid. MS m/e=388 (M+H)+.

Workup

  1. temperatureThe resulting mixture was then cooled to ambient temperature
  2. additionadded to a separatory funnel
  3. custompartitioned with NaHCO3 (saturated, aqueous)
  4. washwashed with NaHCO3 (saturated, aqueous) (2×75 mL)
  5. customseparated
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-1b9416de450840afa76ffe1a720a8542
Source dataset
uspto-grants-2009_12
Patent number
US07635715B2

Reaction notes

Loading…