Benzoylhydrazine → N'-((2R,3S)-2-(2,3-Dichloro-4-cyanophenylamino)-3-hydroxybutanoyl)benzohydrazide

Participants

Role	Name	HCID	Charge
Reactant	Benzoylhydrazine	HCID 11955	—
Reactant	(2R,3S)-2-(2,3-dichloro-4-cyanophenylamino)-3-hydroxybutanoic acid	HCID 57908707	—
Reactant	N'-((2R,3S)-2-(3-chloro-4-cyano-2-ethylphenylamino)-3-hydroxybutanoyl)benzohydrazide	HCID 67007028	—
Product	N'-((2R,3S)-2-(2,3-Dichloro-4-cyanophenylamino)-3-hydroxybutanoyl)benzohydrazide	HCID 57908628	50%

Reaction Steps

(2R,3S)-2-(2,3-dichloro-4-cyanophenylamino)-3-hydroxybutanoic acid (1.0 g, 3.46 mmol) and benzohydrazide (471 mg, 3.46 mmol) were reacted using the techniques described for the preparation of intermediate 11c to furnish the title compound (700 mg, 50%). 1H NMR (500 MHz, acetone-d6, δ in ppm) 9.7 (br s, 2H), 7.91 (d, J=8 Hz, 2H), 7.41-7.62 (m, 4H), 6.82 (d, J=8 Hz, 1H), 6.18 (d, J=7 Hz, 1H), 4.90 (br s, 1H), 4.38-4.41 (m, 1H), 4.19-4.21 (m, 1H) and 1.32 (d, J=6 Hz, 3H).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08268872B2
Source dataset	uspto-grants-2012_09
ORD ID	ord-336d7eb75c5745f9963689c19cdfa586
Source note	uspto-grants-2012_09