HCID 15319065, compound → 1,7-Bis(tert-butoxycarbonylmethyl)-1,4,7,10-tetraazacyclododecane

HRID 531154Notes

Reaction equation

HRID 531154 reaction equation
C(OC([N:11]1[CH2:22][CH2:21][N:20]([CH2:23][C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[CH2:19][CH2:18][N:17](C(OCC2C=CC=CC=2)=O)[CH2:16][CH2:15][N:14]([CH2:41][C:42]([O:44][C:45]([CH3:48])([CH3:47])[CH3:46])=[O:43])[CH2:13][CH2:12]1)=O)C1C=CC=CC=1>C(O)C.[Pd]>[C:24]([CH2:23][N:20]1[CH2:21][CH2:22][NH:11][CH2:12][CH2:13][N:14]([CH2:41][C:42]([O:44][C:45]([CH3:48])([CH3:47])[CH3:46])=[O:43])[CH2:15][CH2:16][NH:17][CH2:18][CH2:19]1)([O:26][C:27]([CH3:28])([CH3:30])[CH3:29])=[O:25]

Participants

4

Reactant 1

HCID 15319065HCID 15319065, compound

Product 1

HCID 3938811,7-Bis(tert-butoxycarbonylmethyl)-1,4,7,10-tetraazacyclododecaneYield 97%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of 7 (8.52 g, 12.74 mmol) in ethanol (130 mL) was added 10% Pd/C (2.6 g). The resulting mixture was stirred under H2 (g) atmosphere at room temperature for 12 hours. The reaction mixture was filtered through a celite pad and washed with ethanol (2×20 mL). The combined filtrate was evaporated in vacuo to give an oily residue which was triturated with Et2O to provide an off-white solid 8 (4.85 g, 97% yield).

Workup

  1. filtrationThe reaction mixture was filtered through a celite pad
  2. washwashed with ethanol (2×20 mL)
  3. customThe combined filtrate was evaporated in vacuo
  4. customto give an oily residue which
  5. customwas triturated with Et2O

Sources & evidence

ORD record
ord-537e630b1f9f4560bebb668a66afc988
Source dataset
uspto-grants-2016_05
Patent number
US09353120B2

Reaction notes

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