Water → 1-Azido-13-oxo-3,6,9,15-tetraoxa-12-azaheptadecan-17-oic acid

HRID 1670374Notes

Reaction equation

HRID 1670374 reaction equation
[N:1]([CH2:4][CH2:5][O:6][CH2:7][CH2:8][O:9][CH2:10][CH2:11][O:12][CH2:13][CH2:14][NH2:15])=[N+:2]=[N-:3].[C:16]1(=[O:23])[O:22][C:20](=[O:21])[CH2:19][O:18][CH2:17]1.O.C(#N)C>ClCCl>[N:1]([CH2:4][CH2:5][O:6][CH2:7][CH2:8][O:9][CH2:10][CH2:11][O:12][CH2:13][CH2:14][NH:15][C:20](=[O:21])[CH2:19][O:18][CH2:17][C:16]([OH:23])=[O:22])=[N+:2]=[N-:3]

Participants

6

Reactant 4

HCID 962WaterHCID 6342AcetonitrileHCID 782321,4-Dioxane-2,6-dioneHCID 27352801-Amino-11-azido-3,6,9-trioxaundecane

Product 1

HCID 713579901-Azido-13-oxo-3,6,9,15-tetraoxa-12-azaheptadecan-17-oic acid

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 11-azido-3,6,9-trioxaundecanamine (10.9 g, 50.0 mmol) in dichloromethane (100 ml) was added diglycolic anhydride (6.38 g, 55.0 mmol). The reaction mixture was stirred overnight. HPLC analysis (column Vydac 218TP54; solvents: A=water/0.1% TFA and B=acetonitrile/0.1% TFA; gradient 4-16% B over 20 min; flow 1.0 ml/min; UV detection at 214 and 284 nm), showed complete conversion of starting material to a product with retention time 18.3 min. The solution was concentrated to give quantitative yield of a yellow syrup. The product was analysed by LC-MS (ES ionisation) giving [MH]+ at 335 as expected. 1H (500 MHz) and 13C (125 MHz) NMR spectroscopy was in agreement with structure The product was used in the next step without further purification.

Workup

  1. waitgradient 4-16% B over 20 min
  2. concentrationThe solution was concentrated

Sources & evidence

ORD record
ord-3e55ba9584054f87bbe6ccf4960683f1
Source dataset
uspto-grants-2011_08
Patent number
US07994134B2

Reaction notes

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