Diethyl Ether → 1,7-Bis(tert-butoxycarbonylmethyl)-1,4,7,10-tetraazacyclododecane

HRID 1523112Notes

Reaction equation

HRID 1523112 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.CCOCC>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

5

Reactant 2

HCID 3283Diethyl EtherHCID 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 compound (19) (8.52 g, 12.74 mmol) in ethanol (130 ml) was added 10% Pd/C (2.6 g). The resultant mixture was stirred at an ambient temperature in the presence of H2 (g) for 12 hours. The reaction mixture was filtered through a celite pad and washed with ethanol (2×20 ml). The filtrate was evaporated in vacuo to give an oily residue, which was then treated with Et2O to obtain a white solid of compound (20) (4.85 g, 97% yield). 1H NMR (500 MHz, CD3OD): δ 3.44 (s, 4H), 2.91 (s, 16H), 1.47 (s, 18H); 13C NMR (125 MHz, CD3OD): δ 173.0, 82.8, 57.4, 52.2, 46.5, 28.5; HRMS (FAB) calculated for C20H41N4O4: 401.3128 [(M+H)+], measured value: 401.3132 [(M+1-1)+].

Workup

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

Sources & evidence

ORD record
ord-b38760f787f8402b8713b1687b3f76bd
Source dataset
uspto-grants-2015_07
Patent number
US09079867B2

Reaction notes

Loading…