4-Chlorobenzohydrazide → 4-Chloro-N'-((2R,3S)-2-(2,3-dichloro-4-cyanophenylamino)-3-hydroxybutanoyl)benzohydrazide

HRID 563241Notes

Reaction equation

HRID 563241 reaction equation
[Cl:1][C:2]1[C:7]([Cl:8])=[C:6]([C:9]#[N:10])[CH:5]=[CH:4][C:3]=1[NH:11][C@H:12]([C@@H:16]([OH:18])[CH3:17])[C:13]([OH:15])=O.[Cl:19][C:20]1[CH:29]=[CH:28][C:23]([C:24]([NH:26][NH2:27])=[O:25])=[CH:22][CH:21]=1.ClC1C(CC)=C(N[C@H]([C@@H](O)C)C(NNC(=O)C2C=CC=CC=2)=O)C=CC=1C#N>>[Cl:19][C:20]1[CH:29]=[CH:28][C:23]([C:24]([NH:26][NH:27][C:13](=[O:15])[C@H:12]([NH:11][C:3]2[CH:4]=[CH:5][C:6]([C:9]#[N:10])=[C:7]([Cl:8])[C:2]=2[Cl:1])[C@@H:16]([OH:18])[CH3:17])=[O:25])=[CH:22][CH:21]=1

Participants

4

Reactant 3

HCID 108164-ChlorobenzohydrazideHCID 57908707(2R,3S)-2-(2,3-dichloro-4-cyanophenylamino)-3-hydroxybutanoic acidHCID 67007028N'-((2R,3S)-2-(3-chloro-4-cyano-2-ethylphenylamino)-3-hydroxybutanoyl)benzohydrazide

Product 1

HCID 579086434-Chloro-N'-((2R,3S)-2-(2,3-dichloro-4-cyanophenylamino)-3-hydroxybutanoyl)benzohydrazideYield 52.3%

Procedure

(2R,3S)-2-(2,3-dichloro-4-cyanophenylamino)-3-hydroxybutanoic acid (1.0 g, 3.46 mmol) and 4-chlorobenzohydrazide (590 mg, 3.46 mmol) were reacted using the techniques described for the preparation of intermediate 11c to furnish the title compound (800 mg, 52%). 1H NMR (500 MHz, acetone-d6, δ in ppm) 10.4 (br s, 2H), 7.98 (d, J=8 Hz, 2H), 7.61 (d, J=8 Hz, 1H), 7.43 (d, J=8 Hz, 2H), 6.84 (d, J=8 Hz, 1H), 6.18 (d, J=6 Hz, 1H), 5.0 (br s, 1H), 4.31-4.38 (m, 1H), 4.18-4.2 (m, 1H), 1.36 (d, J=6 Hz, 3H).

Sources & evidence

ORD record
ord-7e37bc9dfc9846a78dc502e42376ae84
Source dataset
uspto-grants-2011_11
Patent number
US08067448B2

Reaction notes

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