m-Hydroxybenzohydrazide → N'-((2R,3S)-2-(3-chloro-4-cyano-2-methylphenylamino)-3-hydroxybutanoyl)-3-hydroxy-benzohydrazide

HRID 470742

Reaction equation

HRID 470742 reaction equation
[Cl:1][C:2]1[C:3]([CH3:27])=[C:4]([NH:10][C@H:11]([C@@H:24]([OH:26])[CH3:25])[C:12]([NH:14][NH:15][C:16](=[O:23])[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[O:13])[CH:5]=[CH:6][C:7]=1[C:8]#[N:9].ClC1C(C)=C(N[C@H]([C@@H](O)C)C(O)=[O:40])C=CC=1C#N.OC1C=C(C=CC=1)C(NN)=O>CCOC(C)=O>[Cl:1][C:2]1[C:3]([CH3:27])=[C:4]([NH:10][C@H:11]([C@@H:24]([OH:26])[CH3:25])[C:12]([NH:14][NH:15][C:16](=[O:23])[C:17]2[CH:18]=[CH:19][CH:20]=[C:21]([OH:40])[CH:22]=2)=[O:13])[CH:5]=[CH:6][C:7]=1[C:8]#[N:9]

Participants

5

Reactant 3

HCID 79889m-HydroxybenzohydrazideHCID 57908671(3-Chloro-4-cyano-2-methylphenyl)-D-threonine2×HCID 67006523N'-((2R,3S)-2-(3-chloro-4-cyano-2-methylphenylamino)-3-hydroxybutanoyl)benzohydrazide

Product 1

HCID 67005844N'-((2R,3S)-2-(3-chloro-4-cyano-2-methylphenylamino)-3-hydroxybutanoyl)-3-hydroxy-benzohydrazide

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Intermediate 7a was synthesized similarly to the procedure outlined for intermediate 1b described above using (2R,3S)-2-(3-chloro-4-cyano-2-methylphenylamino)-3-hydroxybutanoic acid (intermediate 1a) (522 mg, 1.9 mmol) and 3-hydroxy-benzohydrazide (296 mg, 1.9 mmol). After column chromatography (EtOAc), the title compound was isolated as a white solid (407 mg, 52%). 1H NMR (400 MHz, acetone-d6, δ in ppm) 9.80 (br s, 1H), 9.52 (br s, 1H), 8.76 (br s, 1H), 7.49 (d, J=8.7 Hz, 1 H), 7.40 (m, 1H), 7.29 (at, J=8.1 Hz, 1H), 7.04 (m, 1H), 6.66 (d, J=8.7 Hz, 1H), 5.55 (d, J=7.1 Hz, 1H), 4.89 (br s, 1H), 4.39 (m, 1H), 4.11 (dd, J=3.3, 7.0 Hz, 1H), 2.35 (s, 3H), 1.34 (d, J=6.5 Hz, 3H).

Workup

  1. customIntermediate 7a was synthesized similarly to the procedure

Sources & evidence

ORD record
ord-c29d1ddbac6647838878f78efbb022e7
Source dataset
uspto-grants-2014_01
Patent number
US08629167B2

Linked notes

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