反应 #806288

反应方程式

TBTU

(R)-N-benzyloxycarbonyl-α-carboxy-4-hydroxybenzylamine

(2S)-2-amino butanoic acid t-butyl ester

N-methylmorpholine

→

desired product

收率 63.0%

(R)-N-Benzyloxycarbonyl-α-{N-[(S)-1-(t-butoxycarbonyl)propyl]carbamoyl}-4-hydroxybenzylamine

收率 63.0%

溶剂

DCM

反应条件

后处理

1. 1
   其他The solvent was removed under reduced pressure
2. 2
   其他the residue was purified by flash chromatography on silica gel DCM
3. 3
   其他The product was crystallized from toluene (20 ml)

实验过程

A solution of (R)-N-benzyloxycarbonyl-α-carboxy-4-hydroxybenzylamine (Method 17; 2.00 g, 6.64 mmol), (2S)-2-amino butanoic acid t-butyl ester (1.30 g, 6.64 mmol) and N-methylmorpholine (2.0 g, 19.8 mmol) in DCM (30 ml) was stirred at RT for 5 min, after which TBTU (2.60 g, 8.10 mmol) was added. The reaction mixture was stirred at ambient temperature overnight. The solvent was removed under reduced pressure and the residue was purified by flash chromatography on silica gel DCM:Acetone—60:40). The product was crystallized from toluene (20 ml) giving 1.85 g of the desired product as a white solid. NMR (400 MHz): 0.80 (3H, t), 1.45 (9H, s), 1.50–1.80 (2H, m), 4.10–4.20 (1H, m), 5.05 (1H, d(AB)), 5.15 (1H, d(AB)), 6.75 (2H, d), 7.20–7.40 (7H, m).

来源