Boc-S-benzyl-L-cysteine N-hydroxysuccinimide ester synthesis
- Product Name:Boc-S-benzyl-L-cysteine N-hydroxysuccinimide ester
- CAS Number:3401-33-0
- Molecular formula:C19H24N2O6S
- Molecular Weight:408.47
Yield:3401-33-0 73.3%
Reaction Conditions:
with dicyclohexyl-carbodiimide in 1,4-dioxane;dichloromethane at 0 - 5; for 15 h;
Steps:
Preparation of N-Boc-S-benzyl-L-cysteine-N-succinimidyl ester (Boc-Cys(Bzl)-ONHS)
N-hydroxysuccinimide (2.19 g, 18.72 mmol) was added to a solution ofN-tert-butyloxycarboryl-S-benzyl-L-cysteine (6 g, 19.26 mmol) in 10 mL of anhydrous 1,4-dioxane at25°C. The reaction mixture was cooled to 0°C and then a solution of DCC (4.35 g, 21.18 mmol) in 3 mLof dichloromethane (CH2Cl2) was added slowly and stirred at 5°C for 15 h. After filtration, the solutionwas removed under reduced pressure. The isolated product was recrystallized from isopropanol to yieldBoc-Cys(Bzl)-ONHS as a white solid (6.06 g, 77.0%). 1H NMR (CDCl3) δ/ppm=1.49 (s, 9H), 2.81 (s, 4H),2.9 (m, 2H), 3.80 (s, 2H), 4.80 (m, 1H), 5.24 (d, 1H, J=6.7Hz) and 7.32 (m, 5H). 13C NMR (100 MHz,CDCl3) δ/ppm=171.9, 168.6, 167.3, 154.9, 137.5, 129.2, 128.8, 127.5, 80.9, 77.4, 63.8, 51.7, 36.8, 33.8,28.4, 25.7 and 25.5.
References:
Feng, Wenhua;Li, Xiaobao;Liu, Jinwei;Ma, Chunying;Zheng, Yixuan [Molecules,2022,vol. 27,# 6,art. no. 1920] Location in patent:supporting information
