Phenyl chloroformate → 5-[2-(3-Chloro-phenyl)-ethoxy]-4-ethyl-4H-pyridine-1,3-dicarboxylic acid 3-ethyl ester 1-phenyl ester

HRID 1475763

Reaction equation

[CH2:1]([O:3][C:4](=[O:21])[C:5]1[CH:10]=[C:9]([O:11][CH2:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([Cl:20])[CH:15]=2)[CH:8]=[N:7][CH:6]=1)[CH3:2].Cl[C:23]([O:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)=[O:24].[CH2:32]([Mg]Br)[CH3:33]>C1COCC1>[C:26]1([O:25][C:23]([N:7]2[CH:8]=[C:9]([O:11][CH2:12][CH2:13][C:14]3[CH:19]=[CH:18][CH:17]=[C:16]([Cl:20])[CH:15]=3)[CH:10]([CH2:32][CH3:33])[C:5]([C:4]([O:3][CH2:1][CH3:2])=[O:21])=[CH:6]2)=[O:24])[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Participants

Conditions

Temperature: -30 °C

Procedure

The compound of step 1 (100 mg, 0.327 mmol) was dissolved in THF (1.5 ml) and the mixture was cooled to −30° C. Phenyl chloroformate (77.6 mg, 0.49 mmol) was added and the mixture was stirred for 10 minutes. Ethyl magnesiumbromide (0.589 ml, 1M in THF) was added at −30° C. and the mixture was stirred for 30 minutes, partitioned between diethylether and aqueous ammonium chloride solution, the combined organic extracts were dried over sodium chloride and evaporated to dryness in vacuo. The raw material was purified by silica gel chromatography with a heptane/ethyl acetate gradient to yield the title compound (84 mg).

Workup

stirringthe mixture was stirred for 30 minutes
custompartitioned between diethylether and aqueous ammonium chloride solution
dry with materialthe combined organic extracts were dried over sodium chloride
customevaporated to dryness in vacuo
customThe raw material was purified by silica gel chromatography with a heptane/ethyl acetate gradient

Sources & evidence

ORD record: ord-d1301782727445229f960c00152ae8af
Source dataset: uspto-grants-2015_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09018383B2

Linked notes

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