Acetic Acid → (S)-3-chloro-N-(4-hydroxy-1-(4-(2-(1-(hydroxyimino)ethyl)-1-methyl-1H-imidazol-4-yl)phenyl)butan-2-yl)-4-isopropoxybenzamide

HRID 1436201Notes

Reaction equation

C([O-])(=O)C.[Na+].C(O)(=O)C.[Cl:10][C:11]1[CH:12]=[C:13]([CH:39]=[CH:40][C:41]=1[O:42][CH:43]([CH3:45])[CH3:44])[C:14]([NH:16][C@H:17]([CH2:36][CH2:37][OH:38])[CH2:18][C:19]1[CH:24]=[CH:23][C:22]([C:25]2[N:26]=[C:27]([C:31](=[N:33][O:34]C)[CH3:32])[N:28]([CH3:30])[CH:29]=2)=[CH:21][CH:20]=1)=[O:15].C([O-])(O)=O.[Na+]>O1CCOCC1>[Cl:10][C:11]1[CH:12]=[C:13]([CH:39]=[CH:40][C:41]=1[O:42][CH:43]([CH3:45])[CH3:44])[C:14]([NH:16][C@H:17]([CH2:36][CH2:37][OH:38])[CH2:18][C:19]1[CH:20]=[CH:21][C:22]([C:25]2[N:26]=[C:27]([C:31](=[N:33][OH:34])[CH3:32])[N:28]([CH3:30])[CH:29]=2)=[CH:23][CH:24]=1)=[O:15]

Participants

Conditions

Temperature: 65 °C

Procedure

A mixture of 2-amino-4′-bromoacetophene hydrochloride (10.0 g, 40 mmol), sodium acetate (16.4 g, 200 mmol), acetic acid (11.5 mL, 200 mmol) and compound 2 (19.2 g, 80 mmol) in dioxane (70 mL) was stirred at 65° C. until TLC showed no compound 2 left (about 2 h). The reaction mixture was carefully neutralized with saturated NaHCO3 solution and extracted with ethyl acetate. The organic solution was dried over Na2SO4 and concentrated. Purification with flash column chromatography (EtOAc:Hexs 1:1) gave product 3 (9.11 g, 79%) as a white solid.

Workup

extractionextracted with ethyl acetate
dry with materialThe organic solution was dried over Na2SO4
concentrationconcentrated
customPurification with flash column chromatography (EtOAc:Hexs 1:1)

Sources & evidence

ORD record: ord-79de520767a4497ebe07e7c19a0a9e28
Source dataset: uspto-grants-2009_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07618981B2

Reaction notes

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