Diisopropylethylamine → 1,1-Dimethylethyl N-((6''-chloro-4''-hydroxy-5,5-dimethyl-2''-oxo-dispiro[1,3-dioxane-2,1'-cyclohexane-4',1''-naphthalen]-3''-yl)carbonyl)glycinate

HRID 2078236Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8]1([CH2:16][CH2:15][C:14]3([O:21][CH2:20][C:19]([CH3:23])([CH3:22])[CH2:18][O:17]3)[CH2:13][CH2:12]1)[C:7](=[O:24])[C:6]([C:25](OCC)=[O:26])=[C:5]2[OH:30].Cl.[NH2:32][CH2:33][C:34]([O:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[O:35].C(N(C(C)C)C(C)C)C>O1CCOCC1>[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8]1([CH2:12][CH2:13][C:14]3([O:21][CH2:20][C:19]([CH3:22])([CH3:23])[CH2:18][O:17]3)[CH2:15][CH2:16]1)[C:7](=[O:24])[C:6]([C:25]([NH:32][CH2:33][C:34]([O:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[O:35])=[O:26])=[C:5]2[OH:30]

Participants

Conditions

Temperature: 95 °C

Procedure

A mixture of ethyl 6″-chloro-4″-hydroxy-5,5-dimethyl-2″-oxo-dispiro[1,3-dioxane-2,1′-cyclohexane-4′,1″-naphthalene]-3″-carboxylate (69 mg, 159 μmol) and tert-butyl 2-aminoacetate hydrochloride (53 mg, 317 μmol) in 1.5 mL dioxane was treated with N-ethyl-N-isopropylpropan-2-amine (62 mg, 476 μmol). The mixture was warmed to 95° C. and stirred for 2 hours, M+1=420. The mixture was cooled to room temperature and concentrated in vacuo. The crude product was purified by column chromatography eluting with 10-20% EtOAc/hexane to give 66 mg of the title compound as a white yellow solid. MS (m/z)=520 (M+H)+.

Workup

temperatureThe mixture was cooled to room temperature
concentrationconcentrated in vacuo
customThe crude product was purified by column chromatography
washeluting with 10-20% EtOAc/hexane

Sources & evidence

ORD record: ord-c024857f7fa2435499cb10663f769ae1
Source dataset: uspto-grants-2011_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07928139B2

Reaction notes

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