Diisopropylethylamine → HCID 67100135, compound

HRID 1868626Notes

Reaction equation

HRID 1868626 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:14](=[CH:15][CH:16]=1)[C:8]1([CH2:13][CH2:12][O:11][CH2:10][CH2:9]1)[C:7](=[O:17])[C:6]([C:18](OCC)=[O:19])=[C:5]2[OH:23].Cl.[CH3:25][O:26][C:27](=[O:30])[CH2:28][NH2:29].CCN(C(C)C)C(C)C>O1CCOCC1>[Cl:1][C:2]1[CH:3]=[C:4]2[C:14](=[CH:15][CH:16]=1)[C:8]1([CH2:13][CH2:12][O:11][CH2:10][CH2:9]1)[C:7](=[O:17])[C:6]([C:18]([NH:29][CH2:28][C:27]([O:26][CH3:25])=[O:30])=[O:19])=[C:5]2[OH:23]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 122755Glycine methyl ester hydrochlorideHCID 67099777HCID 67099777, compound

Product 1

HCID 67100135HCID 67100135, compoundYield 74.3%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of ethyl 6-chloro-4-hydroxy-2-oxo-2′,3′,5′,6′-tetrahydro-spiro[naphthalene-1,4′-pyran]-3-carboxylate (0.810 g, 2.41 mmol), glycine methyl ester hydrochloride (0.39 g, 3.11 mmol, 1.3 eq.), 1,4-dioxane (7.0 mL) and DIPEA (1.3 mL, 7.46 mmol) was heated at 80° C. for 6 hours. The mixture was then cooled to room temperature and extracted with EtOAc (3×25 mL). The combined organic extracts were washed with 2N HCl and brine. The solution was dried (MgSO4) and concentrated under reduced pressure to give a pale yellow solid. The product was recrystallized from EtOAc to give a colorless solid (0.68 g). MS m/e=380.0 (M+H)+.

Workup

  1. temperatureThe mixture was then cooled to room temperature
  2. extractionextracted with EtOAc (3×25 mL)
  3. washThe combined organic extracts were washed with 2N HCl and brine
  4. dry with materialThe solution was dried (MgSO4)
  5. concentrationconcentrated under reduced pressure
  6. customto give a pale yellow solid
  7. customThe product was recrystallized from EtOAc

Sources & evidence

ORD record
ord-c46cd342ffdb46d393a381e5cfbd15c4
Source dataset
uspto-grants-2009_12
Patent number
US07635715B2

Reaction notes

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