Methyl Acetate → HCID 117696450, compound

HRID 2205282Notes

Reaction equation

C([Li])CCC.C(NC(C)C)(C)C.[C:13]([NH:17][C:18]([C:20]1[C:25]([CH3:26])=[C:24]([Cl:27])[CH:23]=[CH:22][N:21]=1)=[O:19])([CH3:16])([CH3:15])[CH3:14].[C:28](OC)(=[O:30])[CH3:29].[NH4+].[Cl-]>C1COCC1.C(OCC)(=O)C.O>[C:13]([NH:17][C:18]([C:20]1[C:25]([CH2:26][C:28](=[O:30])[CH3:29])=[C:24]([Cl:27])[CH:23]=[CH:22][N:21]=1)=[O:19])([CH3:16])([CH3:15])[CH3:14]

Participants

Conditions

Temperature: -50 °C

Procedure

n-Butyllithium (2.5 M in hexanes, 28 mL, 70 mmol) is added dropwise to diisopropylamine (10 mL, 70 mmol) in THF (100 mL) at −78° C. After 1 h at −78° C. and 15 min at 0° C. the reaction mixture is cooled to −50° C. and N-tert-butyl-4-chloro-3-methyl-pyridine-2-carboxamide (5.7 g, 25 mmol) in THF (50 mL) is added dropwise and stirring is continued for 30 min at −40° C. Methyl acetate (2.2 mL, 28 mmol) is added and stirring is continued for 30 min at −40° C. Saturated NH4Cl (2 mL), water (6 mL) and ethyl acetate are added and the organic layer is separated, dried and evaporated under reduce pressure to give a residue that is purified by flash chromatography (eluent 0-10% EtOAc/cyclohexane) to furnish 4-chloro-3-(2-oxo-propyl)-pyridine-2-carboxylic acid tert-butylamide (3.7 g, 55%).

Workup

waitis continued for 30 min at −40° C
stirringstirring
waitis continued for 30 min at −40° C
customthe organic layer is separated
customdried
customevaporated
customto give a residue that
customis purified by flash chromatography (eluent 0-10% EtOAc/cyclohexane)

Sources & evidence

ORD record: ord-d962210fda3645edb962d34eedf41dc5
Source dataset: uspto-grants-2016_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09371282B2

Reaction notes

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