tert-Butyl carbazate → 5-(2-(Tert-butoxycarbonyl)hydrazono)-5-(4-fluorophenyl)pentanoic acid

HRID 1803214Notes

Reaction equation

[NH:1]([C:3]([O:5][C:6]([CH3:9])([CH3:8])[CH3:7])=[O:4])[NH2:2].[F:10][C:11]1[CH:16]=[CH:15][C:14]([C:17](=O)[CH2:18][CH2:19][CH2:20][C:21]([OH:23])=[O:22])=[CH:13][CH:12]=1>C1COCC1>[C:6]([O:5][C:3]([NH:1][N:2]=[C:17]([C:14]1[CH:15]=[CH:16][C:11]([F:10])=[CH:12][CH:13]=1)[CH2:18][CH2:19][CH2:20][C:21]([OH:23])=[O:22])=[O:4])([CH3:9])([CH3:8])[CH3:7]

Participants

Conditions

Temperature: 50 °C

Procedure

Step AAG (1): A mixture of tert-butyl hydrazinecarboxylate (1.45 g, 11.0 mmol) and 5-(4-fluorophenyl)-5-oxopentanoic acid (2.1 g, 10 mmol) in THF (20 mL) was stirred at 50° C. for 16 h. The reaction mixture was concentrated in vacuo to afford 5-(2-(tert-butoxycarbonyl)hydrazono)-5-(4-fluorophenyl)pentanoic acid (3.2 g, 9.87 mmol, 99% yield). LC-MS (M+H)+ 325.24. The crude product was used for subsequent chemistry without purification.

Workup

concentrationThe reaction mixture was concentrated in vacuo

Sources & evidence

ORD record: ord-9ef502742c3a4705a70f5d456d1a696b
Source dataset: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08349880B2

Reaction notes

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