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

HRID 408849Notes

Reaction equation

HRID 408849 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([CH2:14][C:15]2[S:16][CH:17]=[C:18]([C:20]([O-:22])=O)[N:19]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[Na+].[C:24]([NH2:28])([CH3:27])([CH3:26])[CH3:25].C(N(CC)CC)C.CCCP1(OP(CCC)(=O)OP(CCC)(=O)O1)=O>ClCCl.C(OCC)(=O)C>[C:24]([NH:28][C:20]([C:18]1[N:19]=[C:15]([CH2:14][N:11]2[CH2:10][CH2:9][N:8]([C:6]([O:5][C:1]([CH3:2])([CH3:4])[CH3:3])=[O:7])[CH2:13][CH2:12]2)[S:16][CH:17]=1)=[O:22])([CH3:27])([CH3:26])[CH3:25]

Participants

7

Reactant 4

HCID 6385Tert-ButylamineHCID 8471TriethylamineHCID 111923Propylphosphonic anhydrideHCID 66661745Sodium 2-((4-(tert-butoxycarbonyl)piperazin-1-yl)methyl)-thiazole-4-carboxylate

Product 1

HCID 66661726tert-Butyl 4-((4-(tert-butylcarbamoyl)thiazol-2-yl)methyl)piperazine-1-carboxylateYield 53.4%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of sodium 2-((4-(tert-butoxycarbonyl)piperazin-1-yl)methyl)-thiazole-4-carboxylate (3.596 g, 10.29 mmol), tert butylamine (0.753 g, 10.29 mmol, 1.082 mL) and triethylamine (3.12 g, 30.9 mmol, 4.29 mL) in dichloromethane (50 mL) was added 1-propanephosphonic acid cyclic anhydride (13.10 g, 20.58 mmol, 12.25 mL, 50% solution in ethyl acetate. The reaction was concentrated under reduced pressure and the residue was taken up in ethyl acetate, washed with sodium bicarbonate (×3) and brine. The organic phase was concentrated under reduced pressure to afford the title compound (2.10 g). MS (ESI) m/z 283.5 [M+H]+

Workup

  1. concentrationThe reaction was concentrated under reduced pressure
  2. washwashed with sodium bicarbonate (×3) and brine
  3. concentrationThe organic phase was concentrated under reduced pressure

Sources & evidence

ORD record
ord-5560e8fb37584396a6913bc6d0dca833
Source dataset
uspto-grants-2014_06
Patent number
US08759352B2

Reaction notes

Loading…