Tert-Butylamine → tert-Butyl 4-((5-(tert-butylcarbamoyl)furan-2-yl)methyl)piperazine-1-carboxylate

HRID 408854Notes

Reaction equation

HRID 408854 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([CH2:14][C:15]2[O:19][C:18]([C:20]([O-:22])=O)=[CH:17][CH:16]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[Na+].[CH3:24][C:25]([NH2:28])([CH3:27])[CH3:26].C(N(CC)CC)C.CCCP1(OP(CCC)(=O)OP(CCC)(=O)O1)=O>ClCCl>[C:25]([NH:28][C:20]([C:18]1[O:19][C:15]([CH2:14][N:11]2[CH2:12][CH2:13][N:8]([C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])[CH2:9][CH2:10]2)=[CH:16][CH:17]=1)=[O:22])([CH3:27])([CH3:26])[CH3:24]

Participants

6

Reactant 4

HCID 6385Tert-ButylamineHCID 8471TriethylamineHCID 111923Propylphosphonic anhydrideHCID 66661312Sodium 5-((4-(tert-butoxycarbonyl)piperazin-1-yl)methyl)furan-2-carboxylate

Product 1

HCID 66661701tert-Butyl 4-((5-(tert-butylcarbamoyl)furan-2-yl)methyl)piperazine-1-carboxylateYield 47.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of sodium 5-((4-(tert-butoxycarbonyl)piperazin-1-yl)methyl)furan-2-carboxylate (4.558 g, 13.72 mmol), 2-methylpropan-2-amine (1.003 g, 13.72 mmol, 1.441 mL) and triethylamine (4.16 g, 41.1 mmol, 5.72 mL) in dichloromethane was added 1-propanephosphonic acid cyclic anhydride (17.46 g, 27.4 mmol, 16.33 mL, 50% solution in ethyl acetate). The reaction was stirred for 2 hours then concentrated under reduced pressure. The residue was taken up in ethyl acetate, washed with sodium bicarbonate, water and brine. The organic phase was concentrated under reduced pressure to give the title compound (2.4 g). MS (ESI) m/z 366.3 [M+H]+

Workup

  1. concentrationthen concentrated under reduced pressure
  2. washwashed with sodium bicarbonate, water and brine
  3. concentrationThe organic phase was concentrated under reduced pressure

Sources & evidence

ORD record
ord-f91211711afe4fb49bce3499470fe826
Source dataset
uspto-grants-2014_06
Patent number
US08759352B2

Reaction notes

Loading…