Pyridine → HCID 18629467, compound

HRID 882379Notes

Reaction equation

HRID 882379 reaction equation
Cl[C:2]([O:4][CH2:5][Cl:6])=[O:3].[CH3:7][O:8][CH2:9][CH2:10][O:11][CH2:12][CH2:13][O:14][CH2:15][CH2:16][OH:17].N1C=CC=CC=1>C(Cl)Cl>[C:2](=[O:3])([O:17][CH2:16][CH2:15][O:14][CH2:13][CH2:12][O:11][CH2:10][CH2:9][O:8][CH3:7])[O:4][CH2:5][Cl:6]

Participants

5

Reactant 3

HCID 1049PyridineHCID 8178Triethylene glycol monomethyl etherHCID 62754Chloromethyl chloroformate

Product 1

HCID 18629467HCID 18629467, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In a manner similar to the method described in Example 3, chloromethyl 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 chloromethyl 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), chiral 3-oxo-2,4,7,10,13-pentaoxatetradecyl 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 C40H47Cl2F2N3O10: [(M+H)+]: 836, found: 836.

Sources & evidence

ORD record
ord-5de0bc258ea844aba7b72337cb7da6fd
Source dataset
uspto-grants-2015_03
Patent number
US08993614B2

Reaction notes

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