4-Methylmorpholine → HCID 9999727, compound

HRID 2375450Notes

Reaction equation

[CH:1]1([C:6]([OH:16])([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[C:7]([OH:9])=O)[CH2:5][CH2:4][CH2:3][CH2:2]1.[CH2:17]([N:24]1[CH2:28][CH2:27][C@H:26]([NH2:29])[CH2:25]1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.CN1CCOCC1.ON1C2C=CC=CC=2N=N1>CN(C)C=O.O>[CH:1]1([C:6]([OH:16])([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[C:7]([NH:29][C@H:26]2[CH2:27][CH2:28][N:24]([CH2:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[CH2:25]2)=[O:9])[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

Conditions

Temperature: 2.5 °C

Procedure

The compound 2-cyclopentyl-2-hydroxy-2-phenylacetic acid (0.52 g, 2.36 mM) and (3S)-1-benzyl-3-aminopyrrolidine (0.5 g, 2.84 mM) were dissolved in dimethylformamide (10.0 ml) and N-methylmorpholine (1.3 ml, 11.8 mM) was added into it followed by the addition of 1-hydroxybenzotriazole (0.32 g, 2.36 mM) at 0-5° C. The reaction mixture was maintained at 0-5° C. for 1 hour and then at room temperature for 19 hours. The reaction mixture was poured into water (100.0 ml) with constant stirring. The organic compound was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated sodium bicarbonate water and brine solution followed its drying and concentration over anhydrous sodium sulphate. The residue was purified by silica gel column chromatography using 10% methanol in chloroform to get the title compound. Yield=95% (0.5 g, 2.38 mM).

Workup

extractionThe organic compound was extracted with ethyl acetate
washThe ethyl acetate layer was washed with saturated sodium bicarbonate water and brine solution
customdrying
concentrationconcentration over anhydrous sodium sulphate
customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record: ord-71cf3078921e45ce96d1fc6b77b826c3
Source dataset: uspto-grants-2008_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07465751B2

Reaction notes

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