Trifluoroacetic acid → HCID 86587441, compound

HRID 1582730Notes

Reaction equation

C(OC([N:8]1[CH2:12][CH2:11][CH2:10][CH:9]1[CH:13]([S:26][CH3:27])[CH2:14][C:15](=[O:25])[NH:16][CH2:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=O)(C)(C)C.[C:28]([OH:34])([C:30]([F:33])([F:32])[F:31])=[O:29]>C(Cl)Cl>[OH:34][C:28]([C:30]([F:33])([F:32])[F:31])=[O:29].[CH3:27][S:26][CH:13]([CH:9]1[CH2:10][CH2:11][CH2:12][NH:8]1)[CH2:14][C:15]([NH:16][CH2:17][CH2:18][C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1)=[O:25]

Participants

Conditions

Temperature: 0 °C

Procedure

To a stirred solution of 2-(1-methylsulfanyl-2-phenethylcarbamoyl-ethyl)-pyrrolidine-1-carboxylic acid tert-butyl ester (1.15 g, 2.93 mmol) in CH2Cl2 (3 ml) was added TFA at 0° C. After being stirred at 0° C. for 30 min, the mixture was evaporated in vacuo to give 3-methylsulfanyl-N-phenethyl-3-pyrrolidin-2-yl-propionamide TFA salt as a crude oil (1.87 g), which was used without further purification in the next step [The diastereomers were separable by preparative HPLC (column: ODS-80Ts, eluent: 79/21 H2O:CH3CN/0.05% TFA)].

Workup

customthe mixture was evaporated in vacuo

Sources & evidence

ORD record: ord-4be086c178e644fc94389388b2d71235
Source dataset: uspto-grants-2004_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06737409B2

Reaction notes

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