Diisopropylethylamine → HCID 54567231, compound

HRID 1060467Notes

Reaction equation

HRID 1060467 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][O:37][CH3:38].Cl.CCN(C(C)C)C(C)C>CCO>[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][O:37][CH3:38])[CH3:33])[CH:19]=1)[NH:6][C:7](=[O:16])[C:8]1[C:9]([Cl:15])=[CH:10][CH:11]=[CH:12][C:13]=1[Cl:14])[CH3:2]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 521874O-Methylhydroxylamine hydrochlorideHCID 541927443-acety-1N-(2,6-dichlorobenzoyl)-4-(2-methoxyphenyl)-L-phenylalanine ethyl ester

Product 1

HCID 54567231HCID 54567231, compoundYield 45.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of N-(2,6-dichlorobenzoyl)-3-acetyl-4-(2-methoxyphenyl)-L-phenylalanine ethyl ester (0.12 g) in EtOH (5 mL) were added NH2OMe HCl salt (24 mg) and DIEA (60 mg). The mixture was refluxed for 2 h and evaporated. The residue was diluted with EtOAc, washed with 1N HCl, dried, and evaporated. The residue was purified by preparative TLC (silica gel; eluent: EtOAc/hexane 2:1)to give 0.058 g of N-(2,6-dichlorobenzoyl)-3-[1-(methoxyimino)ethyl]-4-(2-methoxyphenyl)-L-phenylalanine ethyl ester. ESMS: m/z 534 (M−H)−.

Workup

  1. temperatureThe mixture was refluxed for 2 h
  2. customevaporated
  3. additionThe residue was diluted with EtOAc
  4. washwashed with 1N HCl
  5. customdried
  6. customevaporated
  7. customThe residue was purified by preparative TLC (silica gel

Sources & evidence

ORD record
ord-e533300887ed49d3a5586bf3a8da2541
Source dataset
uspto-grants-2003_02
Patent number
US06521666B1

Reaction notes

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