O-methylhydroxylammonium chloride → (S)-3-chloro-N-(4-hydroxy-1-(4-(2-(1-(methoxyimino)ethyl)-1-methyl-1H-imidazol-4-yl)phenyl)butan-2-yl)-4-isopropoxybenzamide

HRID 1436198Notes

Reaction equation

HRID 1436198 reaction equation
[C:1]([C:4]1[N:5]([CH3:34])[CH:6]=[C:7]([C:9]2[CH:14]=[CH:13][C:12]([CH2:15][C@H:16]([NH:20][C:21](=[O:33])[C:22]3[CH:27]=[CH:26][C:25]([O:28][CH:29]([CH3:31])[CH3:30])=[C:24]([Cl:32])[CH:23]=3)[CH2:17][CH2:18][OH:19])=[CH:11][CH:10]=2)[N:8]=1)(=O)[CH3:2].[CH3:35][O:36][NH3+:37].[Cl-]>N1C=CC=CC=1>[Cl:32][C:24]1[CH:23]=[C:22]([CH:27]=[CH:26][C:25]=1[O:28][CH:29]([CH3:30])[CH3:31])[C:21]([NH:20][C@H:16]([CH2:17][CH2:18][OH:19])[CH2:15][C:12]1[CH:13]=[CH:14][C:9]([C:7]2[N:8]=[C:4]([C:1](=[N:37][O:36][CH3:35])[CH3:2])[N:5]([CH3:34])[CH:6]=2)=[CH:10][CH:11]=1)=[O:33]

Participants

4

Reactant 2

HCID 11639O-methylhydroxylammonium chlorideHCID 57594136(S)-N-(1-(4-(2-acetyl-1-methyl-1H-imidazol-4-yl)phenyl)-4-hydroxybutan-2-yl)-3-chloro-4-isopropoxybenzamide

Product 1

HCID 86604767(S)-3-chloro-N-(4-hydroxy-1-(4-(2-(1-(methoxyimino)ethyl)-1-methyl-1H-imidazol-4-yl)phenyl)butan-2-yl)-4-isopropoxybenzamideYield 70.4%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

80 mg (0.031 mmol) of (S)-N-(1-(4-(2-acetyl-1-methyl-1H-imidazol-4-yl)phenyl)-4-hydroxybutan-2-yl)-3-chloro-4-isopropoxybenzamide in 2 mL of pyridine was treated with 27.6 mg (0.033 mmol) of hydroxylamine methyl ether hydrochloride. The reaction was stirred overnight after which the solvents were evaporated and the residue purified via reverse phase HPLC (acetonitrile/water). 11.2 mg (70% yield) of 2 was obtained and characterized by LCMS and HNMR.

Workup

  1. customwere evaporated
  2. customthe residue purified via reverse phase HPLC (acetonitrile/water)

Sources & evidence

ORD record
ord-a5894666f6684c819f4d6d7e95b063e3
Source dataset
uspto-grants-2009_11
Patent number
US07618981B2

Reaction notes

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