Trifluoroacetic acid → HCID 70024088, compound

HRID 1359030Notes

Reaction equation

[CH3:1][O:2][C:3]([C@@H:5]1[CH2:10][CH2:9][N:8]([S:11]([C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=2)(=[O:13])=[O:12])[C@@H:7]([C:22]([O:24]C(C)(C)C)=[O:23])[CH2:6]1)=[O:4].FC(F)(F)C(O)=O>C(Cl)Cl>[CH3:1][O:2][C:3]([C@@H:5]1[CH2:10][CH2:9][N:8]([S:11]([C:14]2[CH:15]=[CH:16][C:17]([O:20][CH3:21])=[CH:18][CH:19]=2)(=[O:12])=[O:13])[C@@H:7]([C:22]([OH:24])=[O:23])[CH2:6]1)=[O:4]

Participants

Conditions

Temperature: 0 °C

Procedure

To a stirred, cold (0° C.) solution of (2R,4R)-1-(4-methoxy-benzenesulfonyl)-piperidine-2,4-dicarboxylic acid 2-tert-butyl ester 4-methyl ester (4.4 g, 10.6 mmol) in 30 mL of methylene chloride was added 10 mL of trifluoroacetic acid dropwise. The mixture was stirred for 1 hour at 0° C. and for 8 hours at ambient temperature. Concentration provided (2R,4R)-1-(4-methoxy-benzenesulfonyl)-piperidine-2,4-dicarboxylic acid 4-methyl ester, which was used in the subsequent step without purification.

Workup

concentrationConcentration

Sources & evidence

ORD record: ord-9f2266a997904f9f8cb33439f3bffb71
Source dataset: uspto-grants-2003_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06599890B1

Reaction notes

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