Reaction #693770

Reaction equation

4-(2-Amino-acetyl)-benzoic acid methyl ester hydrochloride

NMM

Boc-N-methyl-(L)-alanine

HOBt

WSC.HCl

→

title compound

Yield 73.8%

4-{2-[2-(S)-(tert-Butoxycarbonyl-methyl-amino)-propionylamino]-acetyl}-benzoic acid methyl ester

Yield 73.8%

Solvents

dichloromethane

ethyl acetate

Conditions

Workup

1. 1
   Washwashed with 10% citric acid (2×25 ml) and saturated sodium hydrogen carbonate (2×25 ml)
2. 2
   DryingThe organic layer was dried (MgSO4)
3. 3
   Otherthe solvent removed in vacuo
4. 4
   Otherto give a brown oil residue
5. 5
   OtherPurification by silica chromatography
6. 6
   Washeluting with 10-50% ethyl acetate/iso-hexane

Procedure

4-(2-Amino-acetyl)-benzoic acid methyl ester hydrochloride (2.22 mmol), WSC.HCl (2.44 mmol), Boc-N-methyl-(L)-alanine (2.44 mmol) and HOBt (2.77 mmol) were suspended in dichloromethane (10 ml). NMM (2.44 mmol) was added and the reaction stirred for 2 h. The reaction was diluted with ethyl acetate (50 ml) and washed with 10% citric acid (2×25 ml) and saturated sodium hydrogen carbonate (2×25 ml). The organic layer was dried (MgSO4) and the solvent removed in vacuo to give a brown oil residue. Purification by silica chromatography eluting with 10-50% ethyl acetate/iso-hexane gave the title compound (620 mg) as a pale yellow oil m/z=379 in MS ES+.

Source