tert-Butyldimethylsilyl chloride → 3[4-(t-Butyl-dimethyl-silyloxy)phenyl]2-[(pyridine-3-carbonyl)amino]propionic acid methyl ester

HRID 82479Notes

Reaction equation

[CH3:1][O:2][C:3](=[O:22])[CH:4]([NH:13][C:14]([C:16]1[CH:17]=[N:18][CH:19]=[CH:20][CH:21]=1)=[O:15])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([OH:12])=[CH:8][CH:7]=1.[C:23]([Si:27](Cl)([CH3:29])[CH3:28])([CH3:26])([CH3:25])[CH3:24]>CN(C=O)C>[CH3:1][O:2][C:3](=[O:22])[CH:4]([NH:13][C:14]([C:16]1[CH:17]=[N:18][CH:19]=[CH:20][CH:21]=1)=[O:15])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][Si:27]([C:23]([CH3:26])([CH3:25])[CH3:24])([CH3:29])[CH3:28])=[CH:8][CH:7]=1

Participants

Conditions

Temperature: 25 °C

Procedure

To a solution of 3-(4-hydroxy phenyl)2-[(pyridine-3-carbonyl)amino]propionic acid methyl ester (0.53 g, 1.76 mmol) in DMF (1 mL) was added N,N′-Di isopropyl ethyl amine (0.47 mL, 2.00 mmol) then reaction mixture cooled to (0° C.), t-butyl-dimethyl-silylchloride (0.26 g, 1.76 mmol), was added to reaction mass at (0° C.). The mixture was allowed to stir at room temperature (25° C.) over 5 h. The reaction mixture was quenched with ice, diluted with ethyl acetate (100 mL)), washed with water (3×50 mL) and dried over sodium sulphate. The solvent was evaporated under reduced pressure to obtain product as pale brown liquid (0.6 g, 82%).

Workup

customreaction mixture
additionwas added to reaction mass at (0° C.)
customThe reaction mixture was quenched with ice
additiondiluted with ethyl acetate (100 mL)),
washwashed with water (3×50 mL)
dry with materialdried over sodium sulphate
customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record: ord-d4035612a48848ce84eb4b712aa243f0
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08846721B2

Reaction notes

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