Diisopropylethylamine → HCID 178451285, compound

HRID 1868951Notes

Reaction equation

[Cl:1][C:2]1[CH:16]=[CH:15][CH:14]=[C:13]2[C:3]=1[CH:4]([OH:23])[CH:5]([C:18](OCC)=[O:19])[C:6](=[O:17])[C:7]12[CH2:12][CH2:11][O:10][CH2:9][CH2:8]1.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:5]1[C:4](=[O:23])[C:3]2[C:13](=[CH:14][CH:15]=[CH:16][C:2]=2[Cl:1])[C:7]2([CH2:12][CH2:11][O:10][CH2:9][CH2:8]2)[C:6]=1[OH:17])=[O:19])([CH3:33])([CH3:32])[CH3:31]

Participants

Conditions

Temperature: 95 °C

Procedure

A mixture of ethyl 5-chloro-4-hydroxy-2-oxo-2′,3′,5′,6′-tetrahydro-4H-spiro[naphthalene-1,4′-pyran]-3-carboxylate (70 mg, 208 μmol) and tert-butyl 2-aminoacetate hydrochloride (52 mg, 312 μmol) in 1 mL dioxane was treated with N-ethyl-N-isopropylpropan-2-amine (81 mg, 624 μmol). The mixture was warmed to 95° C. and stirred for 2.5 hours, cooled to room temperature, and then diluted with 20 mL H2O and 100 mL EtOAc. The organic layers were separated, washed with 20 mL 1N HCl×2, water 20 mL, saturated NaCl 20 mL, dried over anhydrous sodium sulfate, and concentrated. The concentrate was purified by column chromatography (10-20% EtOAc/hexane) to give 51 mg pale yellow solid. MS m/e: (M+H)+ 366.

Workup

temperaturecooled to room temperature
customThe organic layers were separated
washwashed with 20 mL 1N HCl×2, water 20 mL, saturated NaCl 20 mL
dry with materialdried over anhydrous sodium sulfate
concentrationconcentrated
customThe concentrate was purified by column chromatography (10-20% EtOAc/hexane)

Sources & evidence

ORD record: ord-23e95eed35af40c5b89cb4d137e836d0
Source dataset: uspto-grants-2009_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07635715B2

Reaction notes

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