Hydroxyamine hydrochloride → N-(2,6-dichlorobenzoyl)-3-[1-(hydroxyimino)ethyl]-4-(2-methoxyphenyl)-L-phenylalanine ethyl ester

HRID 1060466Notes

Reaction equation

HRID 1060466 reaction equation
[CH2:1]([O:3][C:4](=[O:35])[C@H:5]([CH2:17][C:18]1[CH:23]=[CH:22][C:21]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=2[O:30][CH3:31])=[C:20]([C:32](=O)[CH3:33])[CH:19]=1)[NH:6][C:7](=[O:16])[C:8]1[C:13]([Cl:14])=[CH:12][CH:11]=[CH:10][C:9]=1[Cl:15])[CH3:2].[NH2:36][OH:37].Cl.CC([O-])=O.[Na+]>CCCCO>[CH2:1]([O:3][C:4](=[O:35])[C@H:5]([CH2:17][C:18]1[CH:23]=[CH:22][C:21]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=2[O:30][CH3:31])=[C:20]([C:32](=[N:36][OH:37])[CH3:33])[CH:19]=1)[NH:6][C:7](=[O:16])[C:8]1[C:13]([Cl:14])=[CH:12][CH:11]=[CH:10][C:9]=1[Cl:15])[CH3:2]

Participants

5

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 541927443-acety-1N-(2,6-dichlorobenzoyl)-4-(2-methoxyphenyl)-L-phenylalanine ethyl ester

Product 1

HCID 86589923N-(2,6-dichlorobenzoyl)-3-[1-(hydroxyimino)ethyl]-4-(2-methoxyphenyl)-L-phenylalanine ethyl ester

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

To a solution of N-(2,6-dichlorobenzoyl)-3-acetyl-4-(2-methoxyphenyl)-L-phenylalanine ethyl ester (0.15 g) in n-BuOH (5 mL) were added NH2OH HCl salt (23 mg) and NaOAc (40 mg). The mixture was refluxed for 6 hour, then evaporated. The residue was diluted with CH2Cl2, washed with 1N HCl, dried and evaporated. The residue was purified by preparative TLC (silica gel; eluent: EtOAc/hexane 1:1) to give N-(2,6-dichlorobenzoyl)-3-[1-(hydroxyimino)ethyl]-4-(2-methoxyphenyl)-L-phenylalanine ethyl ester. ESMS: m/z 490 (MH+).

Workup

  1. temperatureThe mixture was refluxed for 6 hour
  2. customevaporated
  3. additionThe residue was diluted with CH2Cl2
  4. washwashed with 1N HCl
  5. customdried
  6. customevaporated
  7. customThe residue was purified by preparative TLC (silica gel; eluent: EtOAc/hexane 1:1)

Sources & evidence

ORD record
ord-7842e6f63d9f4aeabfff4738eaab7409
Source dataset
uspto-grants-2003_02
Patent number
US06521666B1

Reaction notes

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