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

HRID 1523102Notes

Reaction equation

HRID 1523102 reaction equation
[C:1]([CH2:8][N:9]1[CH2:22][CH2:21][CH2:20][NH:19][CH2:18][CH2:17][N:16]([CH2:23][C:24]([O:26]C(C)(C)C)=[O:25])[CH2:15][CH2:14][CH2:13][NH:12][CH2:11][CH2:10]1)([O:3]C(C)(C)C)=[O:2].CCOCC>C(C(O)=O)(F)(F)F.C(Cl)Cl>[C:1]([CH2:8][N:9]1[CH2:22][CH2:21][CH2:20][NH:19][CH2:18][CH2:17][N:16]([CH2:23][C:24]([OH:26])=[O:25])[CH2:15][CH2:14][CH2:13][NH:12][CH2:11][CH2:10]1)([OH:3])=[O:2]

Participants

5

Reactant 2

HCID 3283Diethyl EtherHCID 68106176HCID 68106176, compound

Product 1

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

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

Compound (5) (1.12 g, 2.61 mmol) was dissolved in a mixture of CF3CO2H (TFA) and CH2Cl2 (1:1 (v/v), 40 ml). The resultant mixture was stirred at an ambient temperature for 24 hours. The solvent was evaporated under reduced pressure to give an oily residue, which was then treated with Et2O to obtain an off-white solid of compound (6) (1.39 g, 98% yield, calculated as 2 equivalents of TFA for the basic weight). 1H NMR (500 MHz, D2O): δ 3.31 (brs, 2H), 3.22-2.95 (m, 8H), 2.94-2.72 (m, 8H), 2.64 (brs, 2H), 1.83 (brs, 4H); 13C NMR (125 MHz, D2O): δ 180.9, 57.5, 56.9, 55.4, 49.2, 46.2, 23.7; HRMS (FAB) calculated for C14H28N4O4: 317.2189 [(M+H)+], measured value: 317.2185 [(M+H)+].

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. customto give an oily residue, which

Sources & evidence

ORD record
ord-af79c41651744673819633de16bfef64
Source dataset
uspto-grants-2015_07
Patent number
US09079867B2

Reaction notes

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