Trifluoroacetic acid → HCID 68540025, compound

HRID 1994312Notes

Reaction equation

[CH2:1]([N:8]1[CH2:12][CH:11]([CH2:13][C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=2)[N:10]([CH:22]([CH:30]([CH3:32])[CH3:31])[C:23]([O:25]C(C)(C)C)=[O:24])[C:9]1=[O:33])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH2:1]([N:8]1[CH2:12][CH:11]([CH2:13][C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=2)[N:10]([CH:22]([CH:30]([CH3:31])[CH3:32])[C:23]([OH:25])=[O:24])[C:9]1=[O:33])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 0 °C

Procedure

t-Butyl 2-(3-benzyl-5-(4-methoxybenzyl)-2-oxoimidazolidin-1-yl)-3-methylbutyrate (0.22 g; 0.48 mmol) was dissolved in CH2Cl2 (2 ml), and the reaction solution was cooled to 0° C. Then TFA (2 ml) was added. The reaction mixture was stirred at 0° C. for 3 h. It was then concentrated in a rotary evaporator, and the residue was taken up with water and extracted with CH2Cl2 (3×). The organic phase was dried over Na2SO4 and concentrated in a rotary evaporator. 2-(3-Benzyl-5-(4-methoxybenzyl)-2-oxoimidazolidin-1-yl)-3-methylbutyric acid (0.18 g; 0.45 mmol) was obtained as a yellow oil. MS: 397.20 (M+H); Rt: 1.52 min (method: gradient 0 min 96% H2O (0.05% TFA) 2.0 min 95% acetonitrile, 95% acetonitrile to 2.4 min, 4% acetonitrile 2.45 min; flow rate 1 ml/min; column 0.4 μL (YMC J'sphere ODS H80 20X2 1.4μ); 30° C.)

Workup

concentrationIt was then concentrated in a rotary evaporator
extractionextracted with CH2Cl2 (3×)
dry with materialThe organic phase was dried over Na2SO4
concentrationconcentrated in a rotary evaporator

Sources & evidence

ORD record: ord-88f6d7595a024db8943f6daa55b029e6
Source dataset: uspto-grants-2010_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07652143B2

Reaction notes

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