3-Chloro-4-hydroxybenzohydrazide → N'-((2R,3S)-2-(3-Chloro-4-cyano-2-methylphenylamino)-3-hydroxybutanoyl)-3-chloro-4-hydroxybenzohydrazide

HRID 563247Notes

Reaction equation

HRID 563247 reaction equation
[Cl:1][C:2]1[C:3]([CH3:18])=[C:4]([NH:10][C@H:11]([C@@H:15]([OH:17])[CH3:16])[C:12]([OH:14])=O)[CH:5]=[CH:6][C:7]=1[C:8]#[N:9].[Cl:19][C:20]1[CH:21]=[C:22]([CH:27]=[CH:28][C:29]=1[OH:30])[C:23]([NH:25][NH2:26])=[O:24]>>[Cl:1][C:2]1[C:3]([CH3:18])=[C:4]([NH:10][C@H:11]([C@@H:15]([OH:17])[CH3:16])[C:12]([NH:26][NH:25][C:23](=[O:24])[C:22]2[CH:27]=[CH:28][C:29]([OH:30])=[C:20]([Cl:19])[CH:21]=2)=[O:14])[CH:5]=[CH:6][C:7]=1[C:8]#[N:9]

Participants

3

Reactant 2

HCID 109542683-Chloro-4-hydroxybenzohydrazideHCID 57908671(3-Chloro-4-cyano-2-methylphenyl)-D-threonine

Product 1

HCID 67006146N'-((2R,3S)-2-(3-Chloro-4-cyano-2-methylphenylamino)-3-hydroxybutanoyl)-3-chloro-4-hydroxybenzohydrazideYield 82%

Conditions

Temperature
0 °C

Procedure

(2R,3S)-2-(3-chloro-4-cyano-2-methylphenylamino)-3-hydroxybutanoic acid (1.02 g, 3.8 mmol) and 3-chloro-4-hydroxybenzohydrazide (711 mg, 3.8 mmol) were coupled in an analogous fashion as the procedure used for the preparation of intermediate 3b. The crude product was purified by boiling in chloroform (50 mL) followed by cooling to 0° C. and filtration to yield product as a white solid (1.36 g, 82%). 1H NMR (400 MHz, acetone-d6, δ in ppm) 7.93 (d, J=2.2 Hz, 1H), 7.75 (dd, J=2.2, 8.4 Hz, 1H), 7.52 (d, J=8.8 Hz, 1H), 7.08 (d, J=8.6 Hz, 1H), 6.67 (m, 1H), 5.55 (d, J=6.8 Hz, 1H), 4.38 (m, 1H), 4.10 (dd, J=3.1, 7.0 Hz, 1H), 2.36 (s, 3H), 1.34 (d, J=6.5 Hz, 3H).

Workup

  1. customThe crude product was purified
  2. filtrationfiltration

Sources & evidence

ORD record
ord-a5966843db704a2c917de95e43361b8f
Source dataset
uspto-grants-2011_11
Patent number
US08067448B2

Reaction notes

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