Ethyl Acetate → 2-Acetamidoethyl-3-(3-trifluoromethylphenyl)-2-(4-trifluoromethylphenyl)propionate

HRID 2222755Notes

Reaction equation

[F:1][C:2]([F:25])([F:24])[C:3]1[CH:4]=[C:5]([CH2:9][CH:10]([C:14]2[CH:19]=[CH:18][C:17]([C:20]([F:23])([F:22])[F:21])=[CH:16][CH:15]=2)[C:11]([OH:13])=[O:12])[CH:6]=[CH:7][CH:8]=1.C1N=CN(C(N2C=NC=C2)=O)C=1.CCOC(C)=O.[C:44]([NH:47][CH2:48][CH2:49]O)(=[O:46])[CH3:45]>C1COCC1>[C:44]([NH:47][CH2:48][CH2:49][O:12][C:11](=[O:13])[CH:10]([C:14]1[CH:19]=[CH:18][C:17]([C:20]([F:22])([F:23])[F:21])=[CH:16][CH:15]=1)[CH2:9][C:5]1[CH:6]=[CH:7][CH:8]=[C:3]([C:2]([F:24])([F:25])[F:1])[CH:4]=1)(=[O:46])[CH3:45]

Participants

Conditions

Temperature: 23.5 °C

Procedure

3-(3-Trifluoromethylphenyl)-2-(4-trifluoromethylphenyl)-propionic acid (105, 2.43 g, crude) was dissolved in anhydrous THF (6 mL) at ambient temperature. CDI (1.64 g, 10.1 mmol) was charged as a solid, followed by EtOAc (4 mL), to rinse the vial. The internal temperature remained between 20-21° C. during the addition. N-acetylethanolamine (3.6 mL, 39 mmol) was added, whereupon the temperature rose to 24.5° C. The mixture was stirred overnight (16 h) at 23-24° C. and then rotary evaporated to a gummy residue. This was chromatographed on silica gel using EtOAc: hexane (70:30 v/v) (Rf=0.35-0.40) to afford 2-acetamidoethyl-3-(3-trifluoromethylphenyl)-2-(4-trifluoromethylphenyl)propionate 105A (1.85 g).

Workup

washto rinse the vial
additionThe internal temperature remained between 20-21° C. during the addition
customrose to 24.5° C
customrotary evaporated to a gummy residue
customThis was chromatographed on silica gel

Sources & evidence

ORD record: ord-da12e6c83ade428da805a97245743d47
Source dataset: uspto-grants-2008_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07371888B2

Reaction notes

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