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

HRID 24682
Notes
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Reaction equation

HRID 24682 reaction equation
[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]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

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

Product 1

HCID 54520142N-(2,6-dichlorobenzoyl)-4-(2-methoxyphenyl)-L-phenylalanine N-(tert-butyl)-N-hydroxyamide
Yield 65.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

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+).

Workup

  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

Sources & evidence

ORD record
ord-d66f4272403c48259e43dc1b6b2f2af1
Source dataset
uspto-grants-2005_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06855843B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes