Trifluoroacetic acid → Oxo-[2-(2-phenethyl-4-phenyl-butyryl)-piperidin-1-yl]-acetic acid methyl ester

HRID 1828062Notes

Reaction equation

C(OC([N:8]1[CH2:13][CH2:12][CH2:11][CH2:10][CH:9]1[C:14](=[O:32])[CH:15]([CH2:24][CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[CH2:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=O)(C)(C)C.F[C:34](F)(F)C(O)=O.C(N(CC)CC)C.Cl[C:48](=[O:52])[C:49]([O-:51])=[O:50]>C(Cl)Cl>[CH3:34][O:51][C:49](=[O:50])[C:48](=[O:52])[N:8]1[CH2:13][CH2:12][CH2:11][CH2:10][CH:9]1[C:14](=[O:32])[CH:15]([CH2:16][CH2:17][C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1)[CH2:24][CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of 0.24 g (0.55 mmol) of 3 in CH2Cl2 (2 mL) was added dropwise 0.13 mL (1.65 mmol) of trifluoroacetic acid, and the mixture was allowed to stir for 2 hours. The solution was diluted with CH2Cl2 (10 mL) and cooled to 0° C. followed by dropwise addition of 0.3 g (3.00 mmol) of triethylamine. After 5 minutes, to the solution was added dropwise 0.08 g (0.61 mmol) of chlorooxoacetate, and the mixture was stirred for 2 hours. The solution was quenched with H2O and extracted with CH2Cl2 (2×200 mL). The organic phase was dried (MgSO4) and evaporated to a clear oil which was subject to column chromatography (EtOAc/Hexanes, 1:3) to yield 0.19 g (81.9%) of 5 as a clear oil. TLC Rf=0.5 (EtOAc/Hexanes, 1:3)

Workup

waitAfter 5 minutes
stirringthe mixture was stirred for 2 hours
customThe solution was quenched with H2O
extractionextracted with CH2Cl2 (2×200 mL)
dry with materialThe organic phase was dried (MgSO4)
customevaporated to a clear oil which

Sources & evidence

ORD record: ord-16ae2730f60c4713b2a137b6e9a2dd34
Source dataset: uspto-grants-2006_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07056935B2

Reaction notes

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