Triethylamine → 5,9-Bis(benzyloxymethyl)-1-oxa-4,7,10-triazacyclododecane-3,11-dione

HRID 37055

Reaction equation

HRID 37055 reaction equation
[NH2:1][CH:2]([CH2:17][O:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[CH2:3][NH:4][CH2:5][CH:6]([NH2:16])[CH2:7][O:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.C(N(CC)CC)C.[C:33](Cl)(=[O:40])[CH2:34][O:35][CH2:36][C:37](Cl)=[O:38]>ClCCl>[CH2:19]([O:18][CH2:17][CH:2]1[CH2:3][NH:4][CH2:5][CH:6]([CH2:7][O:8][CH2:9][C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=2)[NH:16][C:37](=[O:38])[CH2:36][O:35][CH2:34][C:33](=[O:40])[NH:1]1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 88769Oxydiacetyl dichlorideHCID 194385191,5-Diamino-1,5-dibenzyloxymethyl-3-azapentane

Product 1

HCID 194385105,9-Bis(benzyloxymethyl)-1-oxa-4,7,10-triazacyclododecane-3,11-dione

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

A solution of 1,5-diamino-1,5-dibenzyloxymethyl-3-aza-pentane (0.57 g, 1.7 mmol) (Example 6 (d)) and triethylamine (0.34 g, 3.4 mmol) in dichloromethane (10 ml) and a solution of diglycolic acid dichloride (0.29 g, 1.7 mmol) in dichloromethane (10 ml) were added simultaneously over 2.5 hours to vigorously stirred dichloromethane (10 ml) at 0° C. The solution was stirred at ambient temperature overnight, washed with water (2×30 ml), dried with sodium sulphate and evaporated. Yield 0.59 g (78%).

Workup

  1. washwashed with water (2×30 ml)
  2. dry with materialdried with sodium sulphate
  3. customevaporated

Sources & evidence

ORD record
ord-94e1299595a04e2bbe8fa4673d57ede2
Source dataset
uspto-grants-1995_05
Patent number
US05419893

Linked notes

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