Diisopropylcarbodiimide → {2-[2-({2-[2-(3,4,5,6-Tetraacetoxy-7-hydroxy-2-oxo-heptyloxy)ethoxy]ethylcarbamoyl}methoxy)ethoxy]ethoxy}acetic acid

HRID 2104902

Reaction equation

HRID 2104902 reaction equation
[C:1]([O:4][CH:5]([C:23](=[O:32])[CH2:24][O:25][CH2:26][CH2:27][O:28][CH2:29][CH2:30][NH2:31])[CH:6]([O:19][C:20](=[O:22])[CH3:21])[CH:7]([O:15][C:16](=[O:18])[CH3:17])[CH:8]([O:11][C:12](=[O:14])[CH3:13])[CH2:9][OH:10])(=[O:3])[CH3:2].[C:33]([CH2:36][O:37][CH2:38][CH2:39][O:40][CH2:41][CH2:42][O:43][CH2:44][C:45](O)=[O:46])([OH:35])=[O:34].C(N=C=NC(C)C)(C)C.OC1C2N=NNC=2C=CC=1>C(Cl)Cl>[C:1]([O:4][CH:5]([CH:6]([O:19][C:20](=[O:22])[CH3:21])[CH:7]([O:15][C:16](=[O:18])[CH3:17])[CH:8]([O:11][C:12](=[O:14])[CH3:13])[CH2:9][OH:10])[C:23](=[O:32])[CH2:24][O:25][CH2:26][CH2:27][O:28][CH2:29][CH2:30][NH:31][C:45]([CH2:44][O:43][CH2:42][CH2:41][O:40][CH2:39][CH2:38][O:37][CH2:36][C:33]([OH:35])=[O:34])=[O:46])(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 12734DiisopropylcarbodiimideHCID 837933,6,9-Trioxaundecanedioic acidHCID 235935112,3,4-Triacetoxy-1-{2-[2-(2-aminoethoxy)ethoxy]acetyl}-5-hydroxypentyl acetateHCID 178418300HCID 178418300, compound

Product 1

HCID 22252083{2-[2-({2-[2-(3,4,5,6-Tetraacetoxy-7-hydroxy-2-oxo-heptyloxy)ethoxy]ethylcarbamoyl}methoxy)ethoxy]ethoxy}acetic acid

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 500 mg of 2,3,4-triacetoxy-1-{2-[2-(2-aminoethoxy)ethoxy]acetyl}5 hydroxypentyl acetate 23, 1.15 g of [2-(2-carboxymethoxyethoxy)ethoxy]acetic acid, 400 μl of diisopropylcarbodiimide and 288 mg of hydroxybenzotriazole in 20 ml of methylene chloride is stirred at room temperature for 12 h. The reaction solution is concentrated and separated by HPLC (Knauer Eurospher-100-10-C18, water (0.1% trifluoroacetic acid)/acetonitrile (0.1% trifluoroacetic acid)=80/20->10/90). This gives 24: C28H45NO18 (683.67) MS (ESI) 684 (M+H)

Workup

  1. concentrationThe reaction solution is concentrated
  2. customseparated by HPLC (Knauer Eurospher-100-10-C18, water (0.1% trifluoroacetic acid)/acetonitrile (0.1% trifluoroacetic acid)=80/20->10/90)

Sources & evidence

ORD record
ord-387e133f63da4137985ad56607e15fb6
Source dataset
uspto-grants-2009_08
Patent number
US07576200B2

Linked notes

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