Diisopropylethylamine → HCID 67100162, compound

HRID 1868899Notes

Reaction equation

[Cl:1][C:2]1[CH:16]=[C:15]2[C:5]([C:6]([OH:23])=[C:7]([C:18](OCC)=[O:19])[C:8](=[O:17])[C:9]32[CH2:14][CH2:13][O:12][CH2:11][CH2:10]3)=[CH:4][C:3]=1[F:24].C(N(C(C)C)C(C)C)C.Cl.[NH2:35][CH2:36][C:37]([O:39][C:40]([CH3:43])([CH3:42])[CH3:41])=[O:38]>O1CCOCC1.CCOC(C)=O>[Cl:1][C:2]1[CH:16]=[C:15]2[C:5]([C:6]([OH:23])=[C:7]([C:18]([NH:35][CH2:36][C:37]([O:39][C:40]([CH3:43])([CH3:42])[CH3:41])=[O:38])=[O:19])[C:8](=[O:17])[C:9]32[CH2:10][CH2:11][O:12][CH2:13][CH2:14]3)=[CH:4][C:3]=1[F:24]

Participants

Conditions

Temperature: 80 °C

Procedure

Ethyl 7-chloro-6-fluoro-4-hydroxy-2-oxo-2′,3′,5′,6′-tetrahydro-spiro[naphthalene-1,4′-pyran]-3-carboxylate (580 mg, 1635 μmol) was dissolved in 1,4-dioxane (3270 μL) and N-ethyl-N-isopropylpropan-2-amine (854 μL, 4905 μmol). tert-Butyl 2-aminoacetate hydrochloride (411 mg, 2452 μmol) was added, and the reaction was stirred at 80° C. for 2 hours. The reaction was then diluted with 100 mL of EtOAc, added to a separatory funnel, partitioned with NaHCO3 (saturated, aqueous), washed 2 times with 75 mL of NaHCO3 (saturated, aqueous), separated, dried over Na2SO4, and concentrated in vacuo to give the title (30 mg) compound as a white solid after flash chromatography. MS m/e=440 (M+H)+.

Workup

additionadded to a separatory funnel
custompartitioned with NaHCO3 (saturated, aqueous)
washwashed 2 times with 75 mL of NaHCO3 (saturated, aqueous)
customseparated
dry with materialdried over Na2SO4
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-01c81c69e2e444b2ab7455d606a9b3bc
Source dataset: uspto-grants-2009_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07635715B2

Reaction notes

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