Reaction #531803

ord-a75aad1d06fd48879ecbff38eb160ad4

Reaction equation

Cc1ccccc1C(=O)NC(CC(NC(=O)O)(c1occc(=O)c1OCc1ccccc1)c1occc(=O)c1OCc1ccccc1)c1occc(=O)c1OCc1ccccc1
4c
Cc1ccccc1C(=O)NC(CC(NC(=O)O)(c1occc(=O)c1OCc1ccccc1)c1occc(=O)c1OCc1ccccc1)c1occc(=O)c1OCc1ccccc1
N-(Tris(3-benzyloxy-4-oxo-4H-pyran-2-yl)carboxyaminopropyl)methyl benzamide
Cc1ccccc1C(=O)NC(CC(NC(=O)O)(c1occc(=O)c1O)c1occc(=O)c1O)c1occc(=O)c1O
title compound 6
Yield 114.7%
Cc1ccccc1C(=O)NC(CC(NC(=O)O)(c1occc(=O)c1O)c1occc(=O)c1O)c1occc(=O)c1O
N-(Tris(-3-hydroxy-4-oxo-4H-pyran-2-yl)carboxyaminopropyl)methyl benzamide
Yield 114.7%

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    ConcentrationThe reaction mixture was concentrated in vacuo
  2. 2
    Otherthe residue azeotroped several times with methanol (10 ml)

Procedure

A solution of 4c (0.20 g, 0.20 mmol) in glacial acetic acid (2 ml) and concentrated hydrochloric acid (2 ml) was stirred at room temperature for 18 h. The reaction mixture was concentrated in vacuo, the residue azeotroped several times with methanol (10 ml) to afford the title compound 6 (130 mg, 90%) as a red-orange solid.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US08475768B2uspto-grants-2013_07