Diisopropylethylamine → tert-butyl N-[N-[2-methyl-2-(2,4,6-trimethylphenoxy)propanoyl]carbamimidoyl]carbamate

HRID 873778Notes

Reaction equation

HRID 873778 reaction equation
[C:1]1([CH3:16])[CH:6]=[C:5]([CH3:7])[CH:4]=[C:3]([CH3:8])[C:2]=1[O:9][C:10]([CH3:15])([CH3:14])[C:11]([OH:13])=O.C([N:20](C(C)C)CC)(C)C.N[N:27]([CH:35]=[NH:36])[C:28](=[O:34])[O:29][C:30]([CH3:33])([CH3:32])[CH3:31].O.ON1C2C=CC=CC=2N=N1.F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2C=CC=CC=2N=N1>CN(C)C=O.C(OCC)(=O)C>[NH:20]=[C:35]([NH:27][C:28](=[O:34])[O:29][C:30]([CH3:33])([CH3:32])[CH3:31])[NH:36][C:11](=[O:13])[C:10]([O:9][C:2]1[C:1]([CH3:16])=[CH:6][C:5]([CH3:7])=[CH:4][C:3]=1[CH3:8])([CH3:15])[CH3:14]

Participants

8

Reactant 5

HCID 81531DiisopropylethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 27960291-Hydroxybenzotriazole hydrateHCID 125640962-methyl-2-(2,4,6-trimethylphenoxy)Propanoic acidHCID 86691067Tert-butyl amino(imino)methylcarbamate

Product 1

HCID 149434099tert-butyl N-[N-[2-methyl-2-(2,4,6-trimethylphenoxy)propanoyl]carbamimidoyl]carbamateYield 66.3%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

2-(Mesityloxy)-2-methylpropionic acid (4.45 g; 20 mmol), diisopropylethylamine (12.93 g; 100 mmol), tert-butyl amino(imino)methylcarbamate (3.82 g; 24 mmol), and 1-hydroxybenzotriazole monohydrate (3.68 g; 24 mmol) were dissolved in N,N-dimethylformamide (100 mL), 2-(1H)-benzotriazol-1-yl-1,1,3,3-tetramethyluronium hexafluorophosphate (9.10 g; 24 mmol) was added, and the mixture was stirred for 41 hours at room temperature. To the reaction solution, ethyl acetate (300 mL) was added, and the mixture was washed with 10% aqueous citric acid solution, brine, saturated aqueous sodium bicarbonate solution, and then brine. The organic layer was dried over anhydrous magnesium sulfate and then distilled under reduced pressure. The resulting crystals were dispersed in diisopropyl ether, collected by filtration and dried to give 4.82 g of the title compound (yield 66%).

Workup

  1. washthe mixture was washed with 10% aqueous citric acid solution, brine, saturated aqueous sodium bicarbonate solution
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. distillationdistilled under reduced pressure
  4. additionThe resulting crystals were dispersed in diisopropyl ether
  5. filtrationcollected by filtration
  6. customdried

Sources & evidence

ORD record
ord-c185fc7e81f24f6c87c8222ac8713be7
Source dataset
uspto-grants-2015_03
Patent number
US08975411B2

Reaction notes

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