Diisopropylethylamine → 1,1-Dimethylethyl N-((4-hydroxy-1,1-dimethyl-2-oxo-naphthalen-3-yl)carbonyl)glycinate

HRID 2078201Notes

Reaction equation

[OH:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([CH3:13])([CH3:12])[C:4](=[O:14])[C:3]=1[C:15](OCC)=[O:16].C(N(C(C)C)C(C)C)C.Cl.[NH2:30][CH2:31][C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33]>O1CCOCC1.CCOC(C)=O>[OH:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([CH3:13])([CH3:12])[C:4](=[O:14])[C:3]=1[C:15]([NH:30][CH2:31][C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])=[O:16]

Participants

Conditions

Temperature: 80 °C

Procedure

Ethyl 4-hydroxy-1,1-dimethyl-2-oxo-naphthalene-3-carboxylate (425 mg, 1633 μmol) was dissolved in 1,4-dioxane (1633 μL) and N-ethyl-N-isopropylpropan-2-amine (853 μL, 4898 μmol). tert-Butyl 2-aminoacetate hydrochloride (411 mg, 2449 μmol) was added, and the mixture was heated at 80° C. for 4 hours. The reaction mixture was then cooled, 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 (279 mg) as a white solid after purification via preparatory LC. MS (m/z)=290 (M+H-tBu)+.

Workup

temperatureThe reaction mixture was then cooled
additionadded to a separatory funnel
custompartitioned with NaHCO3 (saturated, aqueous)
washwashed 2 times with 50 mL of NaHCO3 (saturated, aqueous)
customseparated
dry with materialdried over Na2SO4
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-675a1dad53ab459998cd082bbdb61782
Source dataset: uspto-grants-2011_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07928139B2

Reaction notes

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