Water → ethyl (R)-3-[4-(trifluoromethyl) phenylamino]-pentanoate

HRID 1354547Notes

Reaction equation

[CH2:1]([C@H:3]1[N:6]([C:7]2[CH:12]=[CH:11][C:10]([C:13]([F:16])([F:15])[F:14])=[CH:9][CH:8]=2)[C:5](=[O:17])[CH2:4]1)[CH3:2].Cl.[CH2:19](O)[CH3:20].[OH2:22]>C(OCC)(=O)C>[F:14][C:13]([F:16])([F:15])[C:10]1[CH:11]=[CH:12][C:7]([NH:6][C@H:3]([CH2:1][CH3:2])[CH2:4][C:5]([O:17][CH2:19][CH3:20])=[O:22])=[CH:8][CH:9]=1

Participants

Conditions

Temperature: 40 °C

Procedure

To 200 mg (0.822 mmol) of (R)-4-ethyl-1-[4-(trifluoromethyl)phenyl]-2-azetidinone produced in Example 6, 2.0 g (16.45 mmol) of 30 wt % hydrogen chloride/ethanol solution was added dropwise for 5 minutes. On completion of the addition, the resulting solution was heated to 40° C. and stirred for 14 hours. Water (5 mL) was added to the solution and extraction with ethyl acetate was carried out. The extracted organic layer was washed with saturated brine and the product was dried with anhydrous sodium sulfate. The solvent was removed by distillation under reduced pressure to obtain ethyl (R)-3-[4-(trifluoromethyl) phenylamino]-pentanoate as a yellow oil (193.8 mg, crude yield: 82%). 1H-NMR (CDCl3, 400 MHz/ppm): 6 0.98 (3H, t), 1.23 (3H, t), 1.55-1.71 (2H, m), 2.53 (2H, m), 3.75-3.82 (1H, m), 4.11 (2H, q), 6.61 (2H, d), 7.38 (2H, d)

Workup

additionOn completion of the addition
washThe extracted organic layer was washed with saturated brine
dry with materialthe product was dried with anhydrous sodium sulfate
customThe solvent was removed by distillation under reduced pressure

Sources & evidence

ORD record: ord-73fe19ce2e774848ad86095eb599e904
Source dataset: uspto-grants-2007_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07223859B2

Reaction notes

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