1,1'-Dimethyl 2,2'-oxybis(acetate) → 5,9-Bis(benzyloxymethyl)-1-oxa-4,7,10-triazacyclododecane-3,11-dione

HRID 37054

Reaction equation

HRID 37054 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[O:27][C:28](=O)[CH2:29][O:30][CH2:31][C:32](OC)=[O:33]>CO>[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:32](=[O:33])[CH2:31][O:30][CH2:29][C:28](=[O:27])[NH:1]1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

4

Reactant 2

HCID 2018771,1'-Dimethyl 2,2'-oxybis(acetate)HCID 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 887MethanolSolvent

Procedure

1,5 -Diamino-1,5-dibenzyloxymethyl-3 -aza-pentane (0.250 g, 0.73 mmol) (Example 6 (d)) and diglycolic acid dimethyl ester (0.118 g, 0.73 mmol) were dissolved in methanol (20 ml). The mixture was refluxed for 6 days. The solvent was evaporated and the mixture chromatographed on a silica column. 5,9-Bis(benzyloxymethyl)-1-oxa-4,7,10-triazacyclododecane-3,11-dione was isolated as a yellow oil. Yield 0.273 g (85%). FAB MS: 442 (M+1).

Workup

  1. temperatureThe mixture was refluxed for 6 days
  2. customThe solvent was evaporated
  3. customthe mixture chromatographed on a silica column

Sources & evidence

ORD record
ord-3b7234c855c24ff996feb716c9e9cea6
Source dataset
uspto-grants-1995_05
Patent number
US05419893

Linked notes

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