Diethyl Ether → N-(2,6-dichlorobenzoyl)-3-ethyl-4-(2-methoxyphenyl)-L-phenylalanine ethyl ester

HRID 24685Notes

Reaction equation

HRID 24685 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]([CH: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].[SiH](CC)(CC)CC.CCOCC>CC#N>[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]([CH2:32][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 3283Diethyl EtherHCID 12052TriethylsilaneHCID 54510319HCID 54510319, compound

Product 1

HCID 54474420N-(2,6-dichlorobenzoyl)-3-ethyl-4-(2-methoxyphenyl)-L-phenylalanine ethyl esterYield 50.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of N-(2,6-dichlorobenzoyl)-3-(1-hydroxyethyl)-4-(2-methoxyphenyl)-L-phenylalanine ethyl ester (0.08 g) in CH3CN (3 mL) at 0° C. was added Et3SiH (0.075 mL) followed by BE3.Et2O (0.0197 mL). The mixture was warmed to room temperature and stirred for 1 h. The reaction was quenched with CH3OH/H2O and the mixture was extracted with CH2Cl2. The organic layer was dried (MgSO4), filtered and evaporated. The residue was purified by preparative TLC (silica gel; eluent: EtOAc/hexane 1/2) to give 39 mg of N-(2,6-dichlorobenzoyl)-3-ethyl-4-(2-methoxyphenyl)-L-phenylalanine ethyl ester. ESMS: m/z 500 (MH+).

Workup

  1. customThe reaction was quenched with CH3OH/H2O
  2. extractionthe mixture was extracted with CH2Cl2
  3. dry with materialThe organic layer was dried (MgSO4)
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue was purified by preparative TLC (silica gel; eluent: EtOAc/hexane 1/2)

Sources & evidence

ORD record
ord-ba4da33c5c5e4c1d83e22f895c00c9ca
Source dataset
uspto-grants-2005_02
Patent number
US06855843B2

Reaction notes

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