Diisopropylethylamine → N-(2,6-dichlorobenzoyl)-4-(2-methoxyphenyl)-L-phenylalanine N-(tert-butyl)-N-hydroxyamide

HRID 1060454

Reaktionsgleichung

Reaktionsgleichung von HRID 1060454
[Cl:1][C:2]1[CH:29]=[CH:28][CH:27]=[C:26]([Cl:30])[C:3]=1[C:4]([NH:6][C@H:7]([C:23](O)=[O:24])[CH2:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[O:21][CH3:22])=[CH:11][CH:10]=1)=[O:5].[C:31]([NH:35][OH:36])([CH3:34])([CH3:33])[CH3:32].CN([P+](ON1N=NC2C=CC=CC1=2)(N(C)C)N(C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>C(Cl)Cl>[C:31]([N:35]([OH:36])[C:23](=[O:24])[C@H:7]([CH2:8][C:9]1[CH:10]=[CH:11][C:12]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[O:21][CH3:22])=[CH:13][CH:14]=1)[NH:6][C:4](=[O:5])[C:3]1[C:2]([Cl:1])=[CH:29][CH:28]=[CH:27][C:26]=1[Cl:30])([CH3:34])([CH3:33])[CH3:32]

Komponenten

6

Edukt 4

HCID 81531DiisopropylethylamineHCID 98586N-tert-butylhydroxylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 53709169N-(2,6-dichlorobenzoyl)-4-(2-methoxyphenyl)-L-phenylalanine

Produkt 1

HCID 54520142N-(2,6-dichlorobenzoyl)-4-(2-methoxyphenyl)-L-phenylalanine N-(tert-butyl)-N-hydroxyamideAusbeute 65,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of N-(2,6-dichlorobenzoyl)-4-(2-methoxyphenyl)-L-phenylalanine (0.098 g) and tert-butylhydroxylamine (0.047 g) in CH2Cl2 (5 mL) was added BOP reagent (0.17 g) followed by DIEA (0.1 mL) and the mixture was stirred overnight at room temperature. The mixture was evaporated and the residue was dissolved in EtOAc (30 mL). The EtOAc solution was successively washed with 1 N HCl, satd. NaHCO3, satd. LiCl, dried (MgSO4), and concentrated. The residue was purified by preparative TLC (silica gel; eluent: hexane/EtOAc/CH2Cl2 6/1/1) and recrystallization from CH2Cl2/hexane to give 74 mg of N-(2,6-dichlorobenzoyl)-4-(2-methoxyphenyl)-L-phenylalanine N-(tert-butyl)-N-hydroxyamide. ESMS: m/z 515 (MH+).

Aufarbeitung

  1. customThe mixture was evaporated
  2. dissolutionthe residue was dissolved in EtOAc (30 mL)
  3. washThe EtOAc solution was successively washed with 1 N HCl
  4. dry with materialLiCl, dried (MgSO4)
  5. concentrationconcentrated
  6. customThe residue was purified by preparative TLC (silica gel; eluent: hexane/EtOAc/CH2Cl2 6/1/1) and recrystallization from CH2Cl2/hexane

Quellen und Nachweise

ORD-Eintrag
ord-9a40604cb86546019fcd7f1fe1e65e7d
Quelldatensatz
uspto-grants-2003_02
Patentnummer
US06521666B1

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