Dichloromethane → 3-[1-(4-Acetylamino-benzyl)-2-oxo-1,2,5,6-tetrahydro-pyridin-3-yl)-propionic acid methyl ester

HRID 2261396Notes

Reaction equation

[CH3:1][O:2][C:3](=[O:21])[CH2:4][CH2:5][C:6]1[C:7](=[O:20])[N:8]([CH2:12][C:13]2[CH:18]=[CH:17][C:16]([NH2:19])=[CH:15][CH:14]=2)[CH2:9][CH2:10][CH:11]=1.C(Cl)Cl.O(OC(C)=O)[O:26][C:27]([CH3:29])=O.C(N(CC)CC)C>CN(C1C=CN=CC=1)C.CO>[CH3:1][O:2][C:3](=[O:21])[CH2:4][CH2:5][C:6]1[C:7](=[O:20])[N:8]([CH2:12][C:13]2[CH:14]=[CH:15][C:16]([NH:19][C:27](=[O:26])[CH3:29])=[CH:17][CH:18]=2)[CH2:9][CH2:10][CH:11]=1

Participants

Conditions

Temperature: 0 °C

Procedure

17.5 mg of 3-[1-(4-amino-benzyl)-2-oxo-1,2,5,6-tetrahydro-pyridin-3-yl]-propionic acid methyl ester (h) prepared by above Step 1 was dissolved in methylene chloride solution (0.06 mmol). And then 6 μl of (AcO)2O (0.07 mmol), 0.01 ml of triethylamine (0.08 mmol) and 1.0 mg of DMAP (0.008 mmol) were added thereto and the mixture was stirred for 3 hrs at 0° C. The reaction was stopped by adding methanol and the mixture was extracted three times with 10 ml of ethyl acetate. The organic layer was washed with saturated NaCl solution, dried over anhydrous MgSO4, filtered and concentrated in vacuo. The resulting compound was purified with Silica gel column chromatography with ethylacetate as an eluant to give 46 mg of 3-[1-(4-acetylamino-benzyl)-2-oxo-1,2,5,6-tetrahydro-pyridin-3-yl)-propionic acid methyl ester (i) (yield: 44%).

Workup

extractionthe mixture was extracted three times with 10 ml of ethyl acetate
washThe organic layer was washed with saturated NaCl solution
dry with materialdried over anhydrous MgSO4
filtrationfiltered
concentrationconcentrated in vacuo
customThe resulting compound was purified with Silica gel column chromatography with ethylacetate as an eluant

Sources & evidence

ORD record: ord-805b35436e954f028fe9de1a3e60b145
Source dataset: uspto-grants-2010_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07846963B2

Reaction notes

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