4-Nitrobenzoic Acid → HCID 66848190, compound

HRID 536587

Reaction equation

[C:1]([O:5][C:6]([N:8]1[CH2:12][C@H:11]([O:13][Si:14]([C:17]([CH3:20])([CH3:19])[CH3:18])([CH3:16])[CH3:15])[CH2:10][C@H:9]1[CH2:21][OH:22])=[O:7])([CH3:4])([CH3:3])[CH3:2].[N+:23]([C:26]1[CH:34]=[CH:33][C:29]([C:30](O)=[O:31])=[CH:28][CH:27]=1)([O-:25])=[O:24].C1(N=C=NC2CCCCC2)CCCCC1>ClCCl.CN(C)C1C=CN=CC=1>[C:1]([O:5][C:6]([N:8]1[CH2:12][C@H:11]([O:13][Si:14]([C:17]([CH3:20])([CH3:19])[CH3:18])([CH3:16])[CH3:15])[CH2:10][C@H:9]1[CH2:21][O:22][C:30](=[O:31])[C:29]1[CH:28]=[CH:27][C:26]([N+:23]([O-:25])=[O:24])=[CH:34][CH:33]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 0 °C

Procedure

(2S,4R)-4-(Tert-butyl-dimethyl-silanyloxy)-2-hydroxymethyl-pyrrolidine-1-carboxylic acid tert-butyl ester (intermediate 53, 51.4 g, 155 mmol) dissolved in 500 ml of dichloromethane was cooled to 0° C., then p-nitrobenzoic acid (28.5 g, 171 mmol), N,N′-dicyclohexylcarbodiimide (35.2 g, 171 mmol) and 4-dimethylaminopyridine (1.90 g, 1.60 mmol) were added. The mixture was maintained under stirring at room temperature for 18 hours, then filtrated; the filtrate was concentrated to obtain crude that was purified by silica gel chromatography (petroleum ether/ethyl acetate from 15/1 to 10/1). (2S,4R)-4-(tert-Butyl-dimethyl-silanyloxy)-2-(4-nitro-benzoyloxymethyl)-pyrrolidine-1-carboxylic acid tert-butyl ester was obtained as white solid (70 g, yield: 94%).

Workup

temperatureThe mixture was maintained
filtrationfiltrated
concentrationthe filtrate was concentrated
customto obtain crude that
customwas purified by silica gel chromatography (petroleum ether/ethyl acetate from 15/1 to 10/1)

Sources & evidence

ORD record: ord-aedafc3454554af78953524a7ae56442
Source dataset: uspto-grants-2014_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08859608B2

Linked notes

Loading…