L-Phenylalanine → HCID 11153906, compound

Participants

Reaction Steps

To a suspension of 0.467 g of L-phenylalanine and 0.6 g of sodium carbonate in 6 mL of water and 6 mL of dioxane was added dropwise at 0° C. a solution of 1.0 g of succinimidyl 9-xanthenylmethyl carbonate in 10 mL of dioxane over a period of 10 minutes. The mixture was stirred at room temperature for four hours, washed with ether (2×15 mL), and the ether layer was discarded. The aqueous layer was acidified with 10% HCl (Congo Red) and extracted with EtOAc (3×15 ml). The combined organic extracts were dried over MgSO4 and the solvent was evaporated in vacuo to give 1.02 g (89.43%) of the crude Xmoc-Phe-OH as a colorless oil. Crystallization from Skelly B -EtOAc (3:1) gave 0.77 g (67.51%) of the pure Xmoc-Phe-OH as white crystals, m.p. 143°-145° C.; IR KBr: 3420 (NH and OH), 1720 (C=O)cm-1 ; 1H NMR (CDCl3): δ 2.90-3.30 (m, 2H, CH2Ar), 4.40-4.45 (m, 3H, CH--CH2O), 4.65 (m, 1H, NCH), 5.18 (b, 1H, NH), 6.85-7.60 (m, 13H, aryl); [α]23D -3.1 (c=1, EtOAc), [α]23 546 -3.4 (c=1, EtOAc).

Provenance & Evidence