Dimethylformamide → N-[(Phenylmethoxy)carbonyl]-L-tyrosine methyl ester

HRID 583663

Reaction equation

HRID 583663 reaction equation
[C:1]([O-])([O-])=O.[Cs+].[Cs+].[C:7]([NH:17][C@H:18]([C:27]([OH:29])=[O:28])[CH2:19][C:20]1[CH:25]=[CH:24][C:23]([OH:26])=[CH:22][CH:21]=1)([O:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:8].CN(C=O)C.CI>CCOC(C)=O>[CH3:1][O:28][C:27](=[O:29])[C@H:18]([CH2:19][C:20]1[CH:21]=[CH:22][C:23]([OH:26])=[CH:24][CH:25]=1)[NH:17][C:7]([O:9][CH2:10][C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1)=[O:8]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 10796Cesium carbonateHCID 712438N-benzyloxycarbonyl-l-tyrosine

Product 1

HCID 7010613N-[(Phenylmethoxy)carbonyl]-L-tyrosine methyl ester

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A suspension of Cs2CO3 (0.65 g, 2.0 mmol), N-Cbz-L-tyrosine (1.3 g, 4.0 mmol; Bachem) and DMF (40 mL) at ambient temperature was treated with methyl iodide (0.5 mL, 4.0 mmol). After 2.0 h the reaction mixture was diluted with EtOAc and then washed with H2O and brine, dried (MgSO4) and concentrated. Flash chromatography (silica, 25% EtOAc/hexanes) gave 6-4 as a white solid. Rf 0.53 (silica, 50% EtOAc/hexanes).

Workup

  1. washwashed with H2O and brine
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-eb812512c8894e4290944b83353259a2
Source dataset
uspto-grants-1999_07
Patent number
US05929120

Linked notes

Loading…