Hydroxyamine hydrochloride → N-(2,6-dichlorobenzoyl)-4-(2,6-dimethoxyphenyl)-L-phenylalanine N-hydroxyamide

HRID 24681Notes

Reaction equation

HRID 24681 reaction equation
C([O-])(O)=O.[Na+].[NH2:6][OH:7].Cl.[Cl:9][C:10]1[CH:39]=[CH:38][CH:37]=[C:36]([Cl:40])[C:11]=1[C:12]([NH:14][C@H:15]([C:33](Cl)=[O:34])[CH2:16][C:17]1[CH:22]=[CH:21][C:20]([C:23]2[C:28]([O:29][CH3:30])=[CH:27][CH:26]=[CH:25][C:24]=2[O:31][CH3:32])=[CH:19][CH:18]=1)=[O:13]>C1COCC1.O.C1COCC1>[OH:7][NH:6][C:33](=[O:34])[C@H:15]([CH2:16][C:17]1[CH:22]=[CH:21][C:20]([C:23]2[C:28]([O:29][CH3:30])=[CH:27][CH:26]=[CH:25][C:24]=2[O:31][CH3:32])=[CH:19][CH:18]=1)[NH:14][C:12](=[O:13])[C:11]1[C:10]([Cl:9])=[CH:39][CH:38]=[CH:37][C:36]=1[Cl:40]

Participants

6

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 516892Sodium BicarbonateHCID 54238962N(2,6-dichlorobenzoyl)-4-(2,6-dimethoxyphenyl)-L-phenylalanyl chloride

Product 1

HCID 54534956N-(2,6-dichlorobenzoyl)-4-(2,6-dimethoxyphenyl)-L-phenylalanine N-hydroxyamideYield 27.2%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 21881883Oxolane--water (1/1)Solvent

Procedure

NaHCO3 (0.21 g) was added to a solution of NH2OH HCl (0.14 g) in THF/water (5 mL each) at 0° C. and the mixture was stirred for ½ h. A solution of N-(2,6-dichlorobenzoyl)-4-(2,6-dimethoxyphenyl)-L-phenylalanyl chloride (0.1 g) in THF (5 mL) was added to the mixture at 0° C. and the mixture was stirred overnight at room temperature. The mixture was partitioned between EtOAc and water. The EtOAc layer was washed successively with 1 N HCl and brine, dried and evaporated. The residue was purified by preparative TLC (silica gel; eluent: CH2Cl2/MeOH 8%) to yield 27 mg of the title compound. ESMS: m/z 489 (MH+).

Workup

  1. stirringthe mixture was stirred overnight at room temperature
  2. customThe mixture was partitioned between EtOAc and water
  3. washThe EtOAc layer was washed successively with 1 N HCl and brine
  4. customdried
  5. customevaporated
  6. customThe residue was purified by preparative TLC (silica gel; eluent: CH2Cl2/MeOH 8%)

Sources & evidence

ORD record
ord-50c85c0d5c7d4412aec5b631587eb4f9
Source dataset
uspto-grants-2005_02
Patent number
US06855843B2

Reaction notes

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