Potassium Carbonate → 1,4,7-Tris(tert-butoxycarbonylmethyl)-10-((4-tert-butyl)-benzylaminocarbonylmethyl)-1,4,7,10-tetraazacyclodo-decane

HRID 2390752Notes

Reaction equation

HRID 2390752 reaction equation
[C:1]([O:5][C:6]([CH2:8][N:9]1[CH2:20][CH2:19][NH:18][CH2:17][CH2:16][N:15]([CH2:21][C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:14][CH2:13][N:12]([CH2:29][C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])[CH2:11][CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl[CH2:38][C:39]([NH:41][CH2:42][C:43]1[CH:48]=[CH:47][C:46]([C:49]([CH3:52])([CH3:51])[CH3:50])=[CH:45][CH:44]=1)=[O:40].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[C:1]([O:5][C:6]([CH2:8][N:9]1[CH2:20][CH2:19][N:18]([CH2:38][C:39]([NH:41][CH2:42][C:43]2[CH:44]=[CH:45][C:46]([C:49]([CH3:52])([CH3:51])[CH3:50])=[CH:47][CH:48]=2)=[O:40])[CH2:17][CH2:16][N:15]([CH2:21][C:22]([O:24][C:25]([CH3:26])([CH3:27])[CH3:28])=[O:23])[CH2:14][CH2:13][N:12]([CH2:29][C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])[CH2:11][CH2:10]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 11237632Tri-tert-butyl 1,4,7,10-Tetraazacyclododecane-1,4,7-triacetateHCID 46837194HCID 46837194, compound

Product 1

HCID 686362421,4,7-Tris(tert-butoxycarbonylmethyl)-10-((4-tert-butyl)-benzylaminocarbonylmethyl)-1,4,7,10-tetraazacyclodo-decane

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
75 °C

Procedure

A reaction mixture of 1,4,7-tris(tert-butoxycarbonylmethyl)-1,4,7,10-tetraaza-cyclododecane (7.57 g, 12.7 mmol), 2-chloro-N-(4-tert-butylphenylmethyl)-acetamide (3.60 g, 15 mmol) obtained from Example 2a and potassium carbonate (5.53 g, 40 mmol) in acetonitrile (100 ml) was heated to 75° C. and stirred under nitrogen-atmosphere overnight. The reaction mixture was cooled to room temperature and filtered. The filtrate was evaporated in vacuo and the residue was submitted to flash-chromatography (silica, MeOH/CHCl3). The fractions containing the product were combined and evaporated in vacuo resulting in the title compound being a yellow oil that crystallised upon storage.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. filtrationfiltered
  3. customThe filtrate was evaporated in vacuo
  4. additionThe fractions containing the product
  5. customevaporated in vacuo

Sources & evidence

ORD record
ord-65efecc08c5443e98dc9583fadb6e478
Source dataset
uspto-grants-2012_09
Patent number
US08273874B2

Reaction notes

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