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Ethanol → N-Boc-4-cyanophenylalanine-N-methylamide

HRID 1463548
Notes
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Reaction equation

HRID 1463548 reaction equation
[C:1]([NH:8][C@H:9]([C:19]([OH:21])=O)[CH2:10][C:11]1[CH:16]=[CH:15][C:14]([C:17]#[N:18])=[CH:13][CH:12]=1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].FC1C(O)=C(F)C(F)=C(F)C=1F.[CH3:34][N:35]1CCOCC1.C(O)C>C(Cl)Cl>[CH3:34][NH:35][C:19](=[O:21])[C@H:9]([CH2:10][C:11]1[CH:12]=[CH:13][C:14]([C:17]#[N:18])=[CH:15][CH:16]=1)[NH:8][C:1]([O:3][C:4]([CH3:5])([CH3:6])[CH3:7])=[O:2]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 702EthanolHCID 79724-MethylmorpholineHCID 13041PentafluorophenolHCID 7020841N-(tert-Butoxycarbonyl)-4-cyano-L-phenylalanine

Product 1

HCID 22851210N-Boc-4-cyanophenylalanine-N-methylamideYield 92%

Reagents, catalysts & solvents 1

HCID 6344
Dichloromethane
Solvent

Procedure

A solution of N-Boc-4-cyanophenylalanine (1.92 g, 6.6 mmol) and pentafluorophenol (2.43 g, 13.2 mmol) in CH2Cl2 (30 ml) at 0° C. was treated with 4-methylmorpholine (0.74 g, 7.3 mmol). After stirring the reaction mixture for 3 hours, 8M methylazine in ethanol (15 ml, 19.8 mmol) was added and the reaction mixture left to stir at room temperature for 16 hours. The solvent was removed under pressure, the residue dissolved in CH2Cl2 (50 ml) and washed with saturated sodium bicarbonate (2×50 ml) , 1M citric acid (2×50 ml) and brine (50 ml). The CH2Cl2 layer was dried over MgSO4 and the solvent removed under pressure to yield the title compound as a white solid (1.84 g, 92%).

Workup

  1. waitthe reaction mixture left
  2. stirringto stir at room temperature for 16 hours
  3. customThe solvent was removed under pressure
  4. dissolutionthe residue dissolved in CH2Cl2 (50 ml)
  5. washwashed with saturated sodium bicarbonate (2×50 ml) , 1M citric acid (2×50 ml) and brine (50 ml)
  6. dry with materialThe CH2Cl2 layer was dried over MgSO4
  7. customthe solvent removed under pressure

Sources & evidence

ORD record
ord-9949f6ba5f064ab3845911c82f62e8b6
Source dataset
uspto-grants-1994_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05300674

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes