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

HRID 20868Notes

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%).

Workup

temperatureThe mixture was cooled to rt overnight
filtrationthe solid filtered

Sources & evidence

ORD record: ord-7a8e4c5caea948b89050cd9f8014ee26
Source dataset: uspto-grants-2010_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07745636B2

Reaction notes

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