4-(Methylsulfonyl)benzohydrazide → N-((2R,3S)-2-(3-Chloro-4-cyano-2-methylphenylamino)-3-hydroxybutanoyl)-4-(methylsulphonyl)benzohydrazide

HRID 563221Notes

Reaction equation

HRID 563221 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].[CH3:19][S:20]([C:23]1[CH:32]=[CH:31][C:26]([C:27]([NH:29][NH2:30])=[O:28])=[CH:25][CH:24]=1)(=[O:22])=[O:21]>>[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]([N:29]([C:27](=[O:28])[C:26]2[CH:25]=[CH:24][C:23]([S:20]([CH3:19])(=[O:22])=[O:21])=[CH:32][CH:31]=2)[NH2:30])=[O:14])[CH:5]=[CH:6][C:7]=1[C:8]#[N:9]

Participants

3

Reactant 2

HCID 110421074-(Methylsulfonyl)benzohydrazideHCID 57908671(3-Chloro-4-cyano-2-methylphenyl)-D-threonine

Product 1

HCID 67006970N-((2R,3S)-2-(3-Chloro-4-cyano-2-methylphenylamino)-3-hydroxybutanoyl)-4-(methylsulphonyl)benzohydrazideYield 83.2%

Procedure

(2R,3S)-2-(3-chloro-4-cyano-2-methylphenylamino)-3-hydroxybutanoic acid (813 mg, 3.0 mmol) and 4-(methylsulfonyl)benzohydrazide (648 mg, 3.0 mmol) were coupled in a procedure analogous to that described for the preparation of intermediate 3b. The crude product was recrystallized from hotchloroform (100 mL to yield product as a white solid (1.16 g, 82%). 1H NMR (500 MHz, acetone-d6, δ in ppm) 9.83 (br s, 2H), 8.14 (AA′XX′, J=8.5 Hz, 2H), 8.06 (AA′XX′, J=8.5 Hz, 2H), 7.53 (d, J=8.6 Hz, 1H), 6.70 (d, J=8.7 Hz, 1H), 5.57 (d, J=7.0 Hz, 1H), 4.40 (m, 1H), 4.14 (dd, J=3.4, 6.9 Hz, 1H), 3.19 (s, 3H), 2.90 (br s, 1H), 2.36 (s, 3H), 1.36 (d, J=6.4 Hz, 3H).

Workup

  1. customThe crude product was recrystallized from hotchloroform (100 mL

Sources & evidence

ORD record
ord-daf098fca064467899780982b4aab06a
Source dataset
uspto-grants-2011_11
Patent number
US08067448B2

Reaction notes

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