Pyridine → HCID 86696310, compound

HRID 882378Notes

Reaction equation

HRID 882378 reaction equation
Cl[C:2]([O:4][CH:5]([Cl:9])[CH:6]([CH3:8])[CH3:7])=[O:3].[CH3:10][O:11][CH2:12][CH2:13][O:14][CH2:15][CH2:16][O:17][CH2:18][CH2:19][OH:20].N1C=CC=CC=1>C(Cl)Cl>[C:2](=[O:3])([O:20][CH2:19][CH2:18][O:17][CH2:16][CH2:15][O:14][CH2:13][CH2:12][O:11][CH3:10])[O:4][CH:5]([Cl:9])[CH:6]([CH3:8])[CH3:7]

Participants

5

Reactant 3

HCID 1049PyridineHCID 8178Triethylene glycol monomethyl etherHCID 27333261-Chloro-2-Methylpropyl Chloroformate

Product 1

HCID 86696310HCID 86696310, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In a manner similar to the method described in Example 3, 1-chloro-2-methylpropyl chloroformate (Aldrich) was reacted with 2-(2-(2-methoxyethoxy)ethoxy)ethanol (TCI) and pyridine in methylene chloride at −78° C. for 3 h to give 1-chloro-2-methylpropyl 2-(2-(2-methoxyethoxy)-ethoxy)ethyl carbonate. This material was then reacted with chiral 4-((2R,3S,4R,5S)-3-(3-chloro-2-fluorophenyl)-4-(4-chloro-2-fluorophenyl)-4-cyano-5-neopentylpyrrolidine-2-carboxamido)-3-methoxybenzoic acid in the presence of cesium carbonate in dimethylformamide overnight to give, after flash chromatography purification (hexane/ethyl acetate, 80/20 to 20/80), 15-methyl-12-oxo-2,5,8,11,13-pentaoxahexadecan-14-yl 4-((2R,3S,4R,5S)-3-(3-chloro-2-fluorophenyl)-4-(4-chloro-2-fluorophenyl)-4-cyano-5-neopentylpyrrolidine-2-carboxamido)-3-methoxybenzoate as a white solid. MS (ES+) m/z calcd. for C43H52Cl2F2N3O10: [(M+H)+]: 878, found: 878.

Sources & evidence

ORD record
ord-8d900a64f2754efbbd5434402d68d97d
Source dataset
uspto-grants-2015_03
Patent number
US08993614B2

Reaction notes

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