Diisopropylethylamine → HCID 178451287, compound

HRID 1868941Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:16]=1[C:10]1([CH2:15][CH2:14][O:13][CH2:12][CH2:11]1)[C:9](=[O:17])[CH:8]([C:18](OCC)=[O:19])[CH:7]2[OH:23].Cl.[NH2:25][CH2:26][C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28].C(N(C(C)C)C(C)C)C>O1CCOCC1.O.CCOC(C)=O>[C:30]([O:29][C:27](=[O:28])[CH2:26][NH:25][C:18]([C:8]1[C:7](=[O:23])[C:6]2[C:16](=[C:2]([Cl:1])[CH:3]=[CH:4][CH:5]=2)[C:10]2([CH2:11][CH2:12][O:13][CH2:14][CH2:15]2)[C:9]=1[OH:17])=[O:19])([CH3:33])([CH3:32])[CH3:31]

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of ethyl 8-chloro-4-hydroxy-2-oxo-2′,3′,5′,6′-tetrahydro-4H-spiro[naphthalene-1,4′-pyran]-3-carboxylate (0.27 g, 0.80 mmol), and tert-butyl 2-aminoacetate hydrochloride (0.20 g, 1.2 mmol) in 1 mL dioxane was treated with N-ethyl-N-isopropylpropan-2-amine (0.26 g, 2.0 mmol). The mixture was warmed to 100° C. and stirred for 2.5 hours. The mixture was then cooled to room temperature, diluted with 20 mL H2O and 100 mL EtOAc. The organic layer was separated, dried over anhydrous sodium sulfate and concentrated. The concentrate was purified by column chromatography (10-20% EtOAc/hexane) to give 0.13 g off-white solid. MS m/e: (M+H)+ 422.

Workup

temperatureThe mixture was then cooled to room temperature
customThe organic layer was separated
dry with materialdried over anhydrous sodium sulfate
concentrationconcentrated
customThe concentrate was purified by column chromatography (10-20% EtOAc/hexane)

Sources & evidence

ORD record: ord-d0ab9e4afcb4485793ab4ad4d3bb7209
Source dataset: uspto-grants-2009_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07635715B2

Reaction notes

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