Hydrochloric Acid → HCID 11121858, compound

HRID 1374410Notes

Reaction equation

CC(C)([O-])C.[K+].[CH2:7]([O:10][C:11]([N:13]([CH2:29][C:30]([O:32]C)=O)[C@@H:14]([CH2:24][O:25][CH2:26][O:27][CH3:28])[CH2:15][CH2:16][C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])=[O:12])[CH:8]=[CH2:9].Cl.[Cl-].[Na+]>C1COCC1>[CH3:28][O:27][CH2:26][O:25][CH2:24][C@H:14]1[CH2:15][CH:16]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[C:30](=[O:32])[CH2:29][N:13]1[C:11]([O:10][CH2:7][CH:8]=[CH2:9])=[O:12]

Participants

Conditions

Temperature: 0 °C

Procedure

To a suspension of potassium tert-butoxide (299 mg, 2.66 mmol) in THF (26 ml) was added tert-butyl (4R)-4-[[(allyloxy)carbonyl](2-methoxy-2-oxoethyl)amino}-5-(methoxymethoxy)pentanoate (0.52 g, 1.33 mmol) in THF (2.5 ml) and the mixture was stirred for 1 minutes. After cooling to 0° C., the reaction mixture was poured into diluted hydrochloric acid. The solution was adjusted to pH about 3 and after adding a saturated aqueous sodium chloride solution, the solution was extracted with ethyl acetate. The organic layer was washed with water and then a saturated aqueous sodium chloride solution. The organic layer was dried over magnesium sulfate and the organic solvent was removed under reduced pressure. The residue was purified by silica gel (15 g) chromatography (Hexane/ethyl acetate: 3/1) to give 1-allyl 4-tert-butyl (2R)-2-[(methoxymethoxy)methyl]-5-oxo-1,4-piperidinedicarboxylate (0.26 g, 54%).

Workup

extractionthe solution was extracted with ethyl acetate
washThe organic layer was washed with water
dry with materialThe organic layer was dried over magnesium sulfate
customthe organic solvent was removed under reduced pressure
customThe residue was purified by silica gel (15 g) chromatography (Hexane/ethyl acetate: 3/1)

Sources & evidence

ORD record: ord-86c651882f394ec086cc2cb76fbed79c
Source dataset: uspto-grants-2007_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07163936B2

Reaction notes

Loading…