Water → (R)-3-(6-Chloro-3-nitro-pyridin-2-ylamino)-3-phenyl-propionic acid ethyl ester

HRID 2175192

Reaction equation

Cl[C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[C:4]([Cl:11])[N:3]=1.[CH2:12]([O:14][C:15](=[O:25])[CH2:16][C@@H:17]([NH2:24])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[CH3:13].CCN(C(C)C)C(C)C.O>CN(C=O)C.CCOC(C)=O>[CH2:12]([O:14][C:15](=[O:25])[CH2:16][C@@H:17]([NH:24][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[C:4]([Cl:11])[N:3]=1)[C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1)[CH3:13]

Participants

Conditions

Temperature: 70 °C

Procedure

To a solution of 2,6-dichloro-3-nitro-pyridine (0.75 g, 3.58 mmol) in DMF (30 ml) were added (R)-3-amino-3-phenylpropanoic acid ethyl ester (0.83 g, 4.29 mmol) and DIPEA (1.25 ml, 7.15 mmol). The reaction mixture was stirred at 70° C. overnight after which time it was poured into water (200 ml) and EtOAc. The layers were separated and the aqueous phase was extracted once more with EtOAc. The combined organics were washed with water twice and dried (MgSO4). Filtered and concentrated to give the crude product as an orange oil which was then purified by silica gel flash column chromatography (12 g silica gel, 5% EtOAc/Hexane) to afford 0.80 g (64%) of the title compound as a orange oil which was used without further purification.

Workup

customThe layers were separated
extractionthe aqueous phase was extracted once more with EtOAc
washThe combined organics were washed with water twice
dry with materialdried (MgSO4)
filtrationFiltered
concentrationconcentrated
customto give the crude product as an orange oil which
customwas then purified by silica gel flash column chromatography (12 g silica gel, 5% EtOAc/Hexane)

Sources & evidence

ORD record: ord-d06c900b10ad4bcf883d0c15f0078b8d
Source dataset: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09062056B2

Linked notes

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