Diisopropylethylamine → HCID 178485084, compound

HRID 873783Notes

Reaction equation

HRID 873783 reaction equation
[C:1]1([CH3:14])[CH:6]=[C:5]([CH3:7])[CH:4]=[C:3]([CH3:8])[C:2]=1[O:9][CH2:10][C:11]([OH:13])=O.C(N(C(C)C)CC)(C)C.[NH:24]=[C:25]([NH:28][C:29](=[O:35])[O:30][C:31]([CH3:34])([CH3:33])[CH3:32])[NH:26][CH3:27].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>[C:31]([O:30][C:29](=[O:35])[NH:28][C:25](=[N:24][C:11](=[O:13])[CH2:10][O:9][C:2]1[C:1]([CH3:14])=[CH:6][C:5]([CH3:7])=[CH:4][C:3]=1[CH3:8])[NH:26][CH3:27])([CH3:34])([CH3:32])[CH3:33]

Participants

8

Reactant 5

HCID 81531DiisopropylethylamineHCID 8535732-(2,4,6-Trimethylphenoxy)acetic acidHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 27960291-Hydroxybenzotriazole hydrateHCID 178485173HCID 178485173, compound

Product 1

HCID 178485084HCID 178485084, compoundYield 87.3%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

(Mesityloxy)acetic acid (7.77 g; 40 mmol), diisopropylethylamine (25.9 g; 200 mmol), tert-butyl imino(methylamino)methylcarbamate (7.08 g; 41 mmol), and 1-hydroxybenzotriazole monohydrate (7.35 g; 48 mmol) were dissolved in N,N-dimethylformamide (200 mL), 2-(1H)-benzotriazol-1-yl-1,1,3,3-tetramethyluronium hexafluorophosphate (18.2 g; 48 mmol) was added thereto, and the mixture was stirred for 17 hours at room temperature. To the reaction solution, ethyl acetate (400 mL) was added, and the mixture was washed with 10% aqueous citric acid solution, brine, and saturated aqueous sodium bicarbonate solution. The organic layer was dried over anhydrous magnesium sulfate and then distilled under reduced pressure to give 12.2 g of the title compound (yield 87%) as an oil.

Workup

  1. washthe mixture was washed with 10% aqueous citric acid solution, brine, and saturated aqueous sodium bicarbonate solution
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. distillationdistilled under reduced pressure

Sources & evidence

ORD record
ord-470e914838de4101aff5affdc86ecd2c
Source dataset
uspto-grants-2015_03
Patent number
US08975411B2

Reaction notes

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