Diisopropylethylamine → HCID 178451286, compound

HRID 2078364Notes

Reaction equation

HRID 2078364 reaction equation
[F:1][C:2]1[C:16]([F:17])=[C:15]2[C:5]([CH:6]([OH:24])[CH:7]([C:19](OCC)=[O:20])[C:8](=[O:18])[C:9]32[CH2:14][CH2:13][O:12][CH2:11][CH2:10]3)=[CH:4][CH:3]=1.Cl.[NH2:26][CH2:27][C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29].C(N(C(C)C)C(C)C)C>O1CCOCC1.O.CCOC(C)=O>[F:1][C:2]1[C:16]([F:17])=[C:15]2[C:5]([C:6](=[O:24])[C:7]([C:19]([NH:26][CH2:27][C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])=[O:20])=[C:8]([OH:18])[C:9]32[CH2:10][CH2:11][O:12][CH2:13][CH2:14]3)=[CH:4][CH:3]=1

Participants

7

Reactant 3

HCID 81531DiisopropylethylamineHCID 2725036Glycine tert-butyl ester hydrochlorideHCID 67100171HCID 67100171, compound

Product 1

HCID 178451286HCID 178451286, compoundYield 45.2%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of ethyl 7,8-difluoro-4-hydroxy-2-oxo-2′,3′,5′,6′-tetrahydro-4H-spiro[naphthalene-1,4′-pyran]-3-carboxylate (0.23 g, 0.68 mmol), tert-butyl 2-aminoacetate hydrochloride (0.14 g, 0.82 mmol) in 3 mL dioxane was treated with N-ethyl-N-isopropylpropan-2-amine (0.26 g, 2.0 mmol). The mixture was warmed to 120° C. and stirred for 1.5 hours. The mixture was cooled to room temperature, diluted with 20 mL H2O, and 100 mL EtOAc. The organic layer was separated, washed with 20 mL 1N HCl, saturated NH4Cl, dried over anhydrous sodium sulfate and concentrated. The crude product was purified by column chromatography (10-20% EtOAc/hexane) to give 0.13 g white solid. MS m/e: (M+H)+ 424.

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. customThe organic layer was separated
  3. washwashed with 20 mL 1N HCl, saturated NH4Cl
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated
  6. customThe crude product was purified by column chromatography (10-20% EtOAc/hexane)

Sources & evidence

ORD record
ord-2e5facfcc80a42d0bdebb3968ff5de74
Source dataset
uspto-grants-2011_04
Patent number
US07928139B2

Reaction notes

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