1,4,7,10-Tetraazacyclododecane → tert-Butyl (1,4,7,10-tetraazacyclododecan-1-yl)acetate

HRID 480547Notes

Reaction equation

HRID 480547 reaction equation
Br[CH2:2][C:3]([O:5][C:6]([CH3:9])([CH3:8])[CH3:7])=[O:4].[NH:10]1[CH2:21][CH2:20][NH:19][CH2:18][CH2:17][NH:16][CH2:15][CH2:14][NH:13][CH2:12][CH2:11]1>C(Cl)(Cl)Cl>[CH3:7][C:6]([O:5][C:3](=[O:4])[CH2:2][N:10]1[CH2:21][CH2:20][NH:19][CH2:18][CH2:17][NH:16][CH2:15][CH2:14][NH:13][CH2:12][CH2:11]1)([CH3:9])[CH3:8]

Participants

4

Reactant 2

HCID 649631,4,7,10-TetraazacyclododecaneHCID 79177tert-Butyl bromoacetate

Product 1

HCID 15187102tert-Butyl (1,4,7,10-tetraazacyclododecan-1-yl)acetateYield 99.2%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

A solution of t-butyl bromoacetate (25.3 g; 130 mmol) in CHCl3 (500 mL) (commercial product) was added dropwise in 7 h to a solution of 1,4,7,10-tetraazacyclododecane (112.3 g; 650 mmol) (commercial product) in CHCl3 (2 L) maintained under nitrogen at room temperature. After 14 h the solution was concentrated to 800 mL, washed with H2O, dried and evaporated to give the desired compound (39 g; 129 mmol). Yield 99%. GC: 92% (area %). K.F.: 0.42%. The 13C-NMR, MS and IR spectra were consistent with the structure.

Workup

  1. concentrationAfter 14 h the solution was concentrated to 800 mL
  2. washwashed with H2O
  3. customdried
  4. customevaporated

Sources & evidence

ORD record
ord-14049639a5fd4a40a7a050ed3cb12457
Source dataset
uspto-grants-2003_11
Patent number
US06652834B2

Reaction notes

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