Water → 4'-[4-Bromo-5-(hydroxyiminomethyl)-2-propoxy-imidazol-1-ylmethyl]-3'-fluorobiphenyl-2-carboxylic acid t-butyl ester

HRID 1810133Notes

Reaction equation

HRID 1810133 reaction equation
[C:1]([O:5][C:6]([C:8]1[C:9]([C:14]2[CH:19]=[CH:18][C:17]([CH2:20][N:21]3[C:25]([CH:26]=O)=[C:24]([Br:28])[N:23]=[C:22]3[O:29][CH2:30][CH2:31][CH3:32])=[C:16]([F:33])[CH:15]=2)=[CH:10][CH:11]=[CH:12][CH:13]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl.[NH2:35][OH:36].O>N1C=CC=CC=1>[C:1]([O:5][C:6]([C:8]1[C:9]([C:14]2[CH:19]=[CH:18][C:17]([CH2:20][N:21]3[C:25]([CH:26]=[N:35][OH:36])=[C:24]([Br:28])[N:23]=[C:22]3[O:29][CH2:30][CH2:31][CH3:32])=[C:16]([F:33])[CH:15]=2)=[CH:10][CH:11]=[CH:12][CH:13]=1)=[O:7])([CH3:3])([CH3:4])[CH3:2]

Participants

5

Reactant 3

HCID 962WaterHCID 443297Hydroxyamine hydrochlorideHCID 598309054'-(4-Bromo-2-propoxy-5-formylimidazol-1-ylmethyl)-3'-fluorobiphenyl-2-carboxylic acid t-butyl ester

Product 1

HCID 592839014'-[4-Bromo-5-(hydroxyiminomethyl)-2-propoxy-imidazol-1-ylmethyl]-3'-fluorobiphenyl-2-carboxylic acid t-butyl esterYield 86.4%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Compound A (4.5 g) was dissolved in pyridine (80 mL). Hydroxylamine hydrochloride (1.8 g, 26.4 mmol) was added, followed by sufficient water to dissolve the solids. The mixture was stirred at room temperature overnight. The solids were filtered, washed with water, and dried under vacuum to yield compound B (4.0 g).

Workup

  1. dissolutionto dissolve the solids
  2. filtrationThe solids were filtered
  3. washwashed with water
  4. customdried under vacuum

Sources & evidence

ORD record
ord-0d90ff2444704f278c73886bd9ea2f55
Source dataset
uspto-grants-2013_01
Patent number
US08362061B2

Reaction notes

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