Acetic Acid → (S)-tert-Butyl (1-(5-methyl-1,3,4-oxadiazol-2-yl)-2-phenylethyl)carbamate

HRID 339274Notes

Reaction equation

[NH:1]([C:3](=[O:20])[C@@H:4]([NH:12][C:13](=[O:19])[O:14][C:15]([CH3:18])([CH3:17])[CH3:16])[CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[NH2:2].[C:21](OCC)(OCC)(OCC)[CH3:22].CC(O)=O>C1(C)C=CC=CC=1>[CH3:21][C:22]1[O:20][C:3]([C@@H:4]([NH:12][C:13](=[O:19])[O:14][C:15]([CH3:17])([CH3:16])[CH3:18])[CH2:5][C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=2)=[N:1][N:2]=1

Participants

Conditions

Temperature: 80 °C

Procedure

To (S)-tert-butyl (1-hydrazinyl-1-oxo-3-phenylpropan-2-yl)carbamate (120 mg, 0.43 mmol) in PhMe (4.3 mL) was added triethyl orthoacetate (396 μL, 2.15 mmol) and AcOH (443 μL, 7.73 mmol). The resulting solution was stirred at 80° C. for 2 h, then concentrated in vacuo and used in the subsequent step without purification. MS (ESI+) m/z 304.3 (M+H)+.

Workup

concentrationconcentrated in vacuo
customused in the subsequent step without purification

Sources & evidence

ORD record: ord-e36c7e6b23304bfa8a9cfd658b237928
Source dataset: uspto-grants-2014_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08889712B2

Reaction notes

Loading…