Methyl bromoacetate → HCID 57238497, compound

HRID 848929Notes

Reaction equation

HRID 848929 reaction equation
Br.[C:2]([O:6][C:7]([CH2:9][N:10]1[CH2:21][CH2:20][NH:19][CH2:18][CH2:17][N:16]([CH2:22][C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:15][CH2:14][N:13]([CH2:30][C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])[CH2:12][CH2:11]1)=[O:8])([CH3:5])([CH3:4])[CH3:3].Br[CH2:39][C:40]([O:42][CH3:43])=[O:41]>C(#N)C>[C:2]([O:6][C:7]([CH2:9][N:10]1[CH2:21][CH2:20][N:19]([CH2:39][C:40]([O:42][CH3:43])=[O:41])[CH2:18][CH2:17][N:16]([CH2:22][C:23]([O:25][C:26]([CH3:27])([CH3:28])[CH3:29])=[O:24])[CH2:15][CH2:14][N:13]([CH2:30][C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])[CH2:12][CH2:11]1)=[O:8])([CH3:5])([CH3:3])[CH3:4]

Participants

4

Reactant 2

HCID 60984Methyl bromoacetateHCID 21832608Tri-tert-butyl 2,2',2''-(1,4,7,10-tetraazacyclododecane-1,4,7-triyl)triacetate--hydrogen bromide (1/1)

Product 1

HCID 57238497HCID 57238497, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

1,4,7-Tri-tertbutoxycarbonylmethyl-1,4,7,10-tetraazacyclododecane hydrobromide (25.0 g, 42 mmol) was slurried in acetonitrile and treated with TMG (70 mL). Methyl bromoacetate (6.5 g, 42 mmol) was added in one portion, and the mixture was refluxed for 3 hours. After stirring at ambient temperature for an additional 18 hours, the solvent and excess TMG were removed by rotary evaporation. The residue was dissolved in CHCl3, washed with water, and dried (Na2SO4). Evaporation of the solvent afforded the title product as a pale oil (23 g, 95%). 1H NMR (CDCl3): 1.4 (s, 27 H) , 2.8 (s, 16 H), 3.2 (s, 6 H), 3.4 (s 2 H), 3.6 (s, 3 H).

Workup

  1. additiontreated with TMG (70 mL)
  2. temperaturethe mixture was refluxed for 3 hours
  3. customthe solvent and excess TMG were removed by rotary evaporation
  4. dissolutionThe residue was dissolved in CHCl3
  5. washwashed with water
  6. dry with materialdried (Na2SO4)
  7. customEvaporation of the solvent

Sources & evidence

ORD record
ord-fa29adbdc0ae47d1b2f9483f8aaf1629
Source dataset
uspto-grants-2000_01
Patent number
US06010681

Reaction notes

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