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

HRID 1828068Notes

Reaction equation

C(O[C:6]([N:8]1[CH2:12][CH2:11][CH2:10][CH:9]1[C:13](=[O:31])[CH:14]([CH2:23][CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[CH2:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:7])(C)(C)C.FC(F)(F)[C:34]([OH:36])=[O:35].[CH2:39](N(CC)CC)C.ClC(=O)C([O-])=O>C(Cl)Cl>[CH3:39][O:36][C:34](=[O:35])[C:6](=[O:7])[N:8]1[CH2:12][CH2:11][CH2:10][CH:9]1[C:13](=[O:31])[CH:14]([CH2:23][CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[CH2:15][CH2:16][C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of 0.18 g (0.40 mmol) of 11a in CH2Cl2 (3 mL) was added dropwise 10 mL (8.77 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 0.7 g (10.00 mmol) of triethylamine. After 5 minutes, to the solution was added dropwise 0.06 g (0.5 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, 1:1) to yield 0.16 g (98.2%) of 12a as a clear oil. TLC Rf=0.6 (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-f34f3b4973d94bd0a8a050f976f8fc43
Source dataset: uspto-grants-2006_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07056935B2

Reaction notes

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