Diisopropylethylamine → HCID 67100020, compound

HRID 1868889Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]2[C:14](=[CH:15][CH:16]=1)[C:8]1([CH2:13][CH2:12][O:11][CH2:10][CH2:9]1)[C:7](=[O:17])[C:6]([C:18](OCC)=[O:19])=[C:5]2[OH:23].C(N(C(C)C)C(C)C)C.Cl.[CH3:34][O:35][C:36](=[O:41])[C@H:37]([CH2:39][OH:40])[NH2:38]>O1CCOCC1.CCOC(C)=O>[Cl:1][C:2]1[CH:3]=[C:4]2[C:14](=[CH:15][CH:16]=1)[C:8]1([CH2:9][CH2:10][O:11][CH2:12][CH2:13]1)[C:7](=[O:17])[C:6]([C:18]([NH:38][C@H:37]([C:36]([O:35][CH3:34])=[O:41])[CH2:39][OH:40])=[O:19])=[C:5]2[OH:23]

Participants

Conditions

Temperature: 80 °C

Procedure

Ethyl 6-chloro-4-hydroxy-2-oxo-2′,3′,5′,6′-tetrahydro-spiro[naphthalene-1,4′-pyran]-3-carboxylate (287 mg, 852 μmol, Example 1 A-C) was dissolved in 1,4-dioxane (852 μL) and N-ethyl-N-isopropylpropan-2-amine (445 μL, 2557 μmol). L-Serine methyl ester hydrochloride (199 mg, 1278 μmol) was added, and the mixture was stirred at 80° C. for 3 hours. The reaction mixture was then 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 180 mg of the title compound as a white solid after flash chromatography. MS m/e=410 (M+H)+.

Workup

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-20fb55d883d14fcfb971b8a24073219e
Source dataset: uspto-grants-2009_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07635715B2

Reaction notes

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