Diisopropylethylamine → HCID 67100249, compound

HRID 1868786Notes

Reaction equation

HRID 1868786 reaction equation
[OH:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([CH3:12])[CH:10]=2)[C:5]([CH3:14])([CH3:13])[C:4](=[O:15])[C:3]=1[C:16](OCC)=[O:17].C(N(C(C)C)C(C)C)C.Cl.[NH2:31][CH2:32][C:33]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34]>O1CCOCC1.CCOC(C)=O>[CH3:12][C:9]1[CH:10]=[C:11]2[C:6](=[CH:7][CH:8]=1)[C:5]([CH3:13])([CH3:14])[C:4](=[O:15])[C:3]([C:16]([NH:31][CH2:32][C:33]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34])=[O:17])=[C:2]2[OH:1]

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 2725036Glycine tert-butyl ester hydrochlorideHCID 67099332HCID 67099332, compound

Product 1

HCID 67100249HCID 67100249, compoundYield 27.1%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
80 °C

Procedure

Ethyl 4-hydroxy-1,1,6-trimethyl-2-oxo-naphthalene-3-carboxylate (750 mg, 2734 μmol) was dissolved in 1,4-dioxane (2734 μL) and N-ethyl-N-isopropylpropan-2-amine (1429 μL, 8202 μmol). tert-Butyl 2-aminoacetate hydrochloride (687 mg, 4101 μmol) was added, and the reaction was stirred at 80° C. for 1 hour. The reaction mixture was cooled to ambient temperature, 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 (266 mg) as a white solid after flash chromatography. MS (m/z)=304(M+H-tBu)+.

Workup

  1. temperatureThe reaction mixture was cooled to ambient temperature
  2. additionadded to a separatory funnel
  3. custompartitioned with NaHCO3 (saturated, aqueous)
  4. washwashed 2 times with 50 mL of NaHCO3 (saturated, aqueous)
  5. customseparated
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-124ea5279b604ce6a907b7ab88b5a75c
Source dataset
uspto-grants-2009_12
Patent number
US07635715B2

Reaction notes

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