Diisopropylethylamine → HCID 67099579, compound

HRID 1868670Notes

Reaction equation

HRID 1868670 reaction equation
[CH3:1][O:2][C:3]1[CH:17]=[CH:16][CH:15]=[C:14]2[C:4]=1[C:5]([OH:24])=[C:6]([C:19](OCC)=[O:20])[C:7](=[O:18])[C:8]12[CH2:13][CH2:12][O:11][CH2:10][CH2:9]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>[OH:24][C:5]1[C:4]2[C:14](=[CH:15][CH:16]=[CH:17][C:3]=2[O:2][CH3:1])[C:8]2([CH2:13][CH2:12][O:11][CH2:10][CH2:9]2)[C:7](=[O:18])[C:6]=1[C:19]([NH:26][CH2:27][C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])=[O:20]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 2725036Glycine tert-butyl ester hydrochlorideHCID 67099505HCID 67099505, compound

Product 1

HCID 67099579HCID 67099579, compoundYield 63.5%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
86 °C

Procedure

A mixture of ethyl 5-methoxy-4-hydroxy-2-oxo-2′,3′,5′,6′-tetrahydro-spiro[naphthalene-1,4′-pyran]-3-carboxylate (44 mg, 132 μmol), tert-butyl 2-aminoacetate hydrochloride (33 mg, 199 μmol) in 2 mL dioxane was treated with N-ethyl-N-isopropylpropan-2-amine (51 mg, 397 μmol). The mixture was warmed to 86° C. and stirred for 14 hours, M+1=418. The mixture was then cooled to room temperature and concentrated in vacuo. The crude product was purified by column chromatography eluting with 10-30% EtOAc/hexane to give 35 mg of the title compound as a yellow oil. MS (m/z) 418 (M+H)+.

Workup

  1. temperatureThe mixture was then cooled to room temperature
  2. concentrationconcentrated in vacuo
  3. customThe crude product was purified by column chromatography
  4. washeluting with 10-30% EtOAc/hexane

Sources & evidence

ORD record
ord-5f6eafd959234c59a6f409341eb1da78
Source dataset
uspto-grants-2009_12
Patent number
US07635715B2

Reaction notes

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