Pyrazole → (S)-2-(((Benzyloxy)carbonyl)amino)-3-(1H-pyrazol-1-YL)propanoic acid

HRID 1919214Notes

Reaction equation

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

Participants

Conditions

Temperature: 50 °C

Procedure

A suspension of (S)-benzyl 2-oxooxetan-3-ylcarbamate (0.67 g, 3.03 mmol), and pyrazole (0.22 g, 3.29 mmol) in CH3CN (12 mL) was heated at 50° C. for 24 h. The mixture was cooled to rt overnight and the solid filtered to afford (S)-2-(benzyloxycarbonylamino)-3-(1H-pyrazol-1-yl)propanoic acid (330.1 mg). The filtrate was concentrated in vacuo and then triturated with a small amount of CH3CN (ca. 4 mL) to afford a second crop (43.5 mg). Total yield 370.4 mg (44%). m.p. 165.5-168° C. lit m.p. 168.5-169.5 [Vederas et al. J. Am. Chem. Soc. 1985, 107, 7105]. 1H NMR (400 MHz, CD3OD) δ 7.51 (d, J=2.0, 1H), 7.48 (s, J=1.5 Hz, 1H), 7.24-7.34 (m, 5H), 6.23 m, 1H), 5.05 (d, 12.7H, 1H), 5.03 (d, J=12.7 Hz, 1H), 4.59-4.66 (m, 2H), 4.42-4.49 (m, 1H). LCMS: Anal. Calcd. for C14H15N3O4: 289. Found: 290 (M+H)+.

Workup

temperatureThe mixture was cooled to rt overnight
filtrationthe solid filtered

Sources & evidence

ORD record: ord-8dc0ab0a71d4405dab2cdead10c0a309
Source dataset: uspto-grants-2013_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08618153B2

Reaction notes

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