Triethylamine → tert-Butyl 3-(dimethylcarbamoyl)pentan-3-ylcarbamate

HRID 927378Notes

Reaction equation

HRID 927378 reaction equation
[C:1]([O:5][C:6]([NH:8][C:9]([CH2:15][CH3:16])([CH2:13][CH3:14])[C:10](O)=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:17][N:18](C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)[CH3:19].F[P-](F)(F)(F)(F)F.C(N(CC)CC)C.Cl.CNC>CN(C=O)C.O>[CH3:17][N:18]([CH3:19])[C:10]([C:9]([NH:8][C:6](=[O:7])[O:5][C:1]([CH3:4])([CH3:3])[CH3:2])([CH2:15][CH3:16])[CH2:13][CH3:14])=[O:11]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 10473Dimethylamine, hydrochlorideHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 151085042-(((Tert-butoxy)carbonyl)amino)-2-ethylbutanoic acid

Product 1

HCID 86674741tert-Butyl 3-(dimethylcarbamoyl)pentan-3-ylcarbamateYield 53.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

2-(tert-butoxycarbonylamino)-2-ethylbutanoic acid ((200 mg, 0.87 mmol), HATU (CAN 148893-10-1, 660 mg, 1.74 mmol) and triethylamine (CAN 121-44-8, 260 mg, 2.61 mmol) was added to a solution of dimethylamine hydrochloride (CAN 506-59-2, 117 mg, 1.74 mmol) in DMF (10 mL). The mixture was stirred overnight at room temperature. The mixture was added to water (20 mL) and extracted with ethyl acetate (30 mL). The organic extracts were washed with brine, dried over anhydrous sodium sulfate, concentrated, and purified by prep-HPLC (eluting with 30% ethyl acetate in petroleum ether) to give the product (120 mg, 53.7%); MS (EI): m/e=259.2 [M+H]+

Workup

  1. extractionextracted with ethyl acetate (30 mL)
  2. washThe organic extracts were washed with brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated
  5. custompurified by prep-HPLC (eluting with 30% ethyl acetate in petroleum ether)

Sources & evidence

ORD record
ord-b508e1b93e154accaf61316c1fd42050
Source dataset
uspto-grants-2016_03
Patent number
US09290451B2

Reaction notes

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