Diethyl Ether → 2,2'-(1,4,8,11-Tetraazacyclotetradecane-1,8-diyl)diacetic acid

HRID 1523101Notes

Reaction equation

HRID 1523101 reaction equation
C([O:8][C:9]([CH2:11][N:12]1[CH2:25][CH2:24][CH2:23][NH:22][CH2:21][CH2:20][N:19]([CH2:26][C:27]([O:29]CC2C=CC=CC=2)=[O:28])[CH2:18][CH2:17][CH2:16][NH:15][CH2:14][CH2:13]1)=[O:10])C1C=CC=CC=1.C(OCC)C>C(O)C.[Pd]>[C:9]([CH2:11][N:12]1[CH2:25][CH2:24][CH2:23][NH:22][CH2:21][CH2:20][N:19]([CH2:26][C:27]([OH:29])=[O:28])[CH2:18][CH2:17][CH2:16][NH:15][CH2:14][CH2:13]1)([OH:10])=[O:8]

Participants

5

Reactant 2

HCID 3283Diethyl EtherHCID 68106200HCID 68106200, compound

Product 1

HCID 142038522,2'-(1,4,8,11-Tetraazacyclotetradecane-1,8-diyl)diacetic acidYield 98%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of compound (4) (0.48 g, 0.96 mmol) in absolute ethanol (40 ml) was added 10% Pd/C (0.12 g). The resultant mixture was stirred at an ambient temperature under H2 atmosphere for 10 hours. The reaction mixture was filtered through a celite pad, and washed with ethanol (2×10 ml). The combined filtrate was evaporated in vacuo to give an oily residue, which was then treated with diethyl ether (Et2O) to obtain an off-white solid (0.29 g, 98% yield). 1H NMR (500 MHz, D2O): δ 3.48 (brs, 2H), 3.01-3.19 (m, 10H), 2.80 (brs, 6H), 2.67 (brs, 2H), 1.84 (brs, 4H); 13C NMR (125 MHz, D2O): δ 179.0, 56.3, 55.7, 48.9, 45.4, 22.8; HRMS (FAB) calculated for C14H28N4O4: 317.2189 [(M+H)+], measured value: 317.2185 [(M+H)+].

Workup

  1. filtrationThe reaction mixture was filtered through a celite pad
  2. washwashed with ethanol (2×10 ml)
  3. customThe combined filtrate was evaporated in vacuo
  4. customto give an oily residue, which

Sources & evidence

ORD record
ord-0d8e01ab12844f008cb54297f5c046f0
Source dataset
uspto-grants-2015_07
Patent number
US09079867B2

Reaction notes

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