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

HRID 632078Notes

Reaction equation

HRID 632078 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=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(CC)CC.Cl.CN>CN(C=O)C.O>[CH3:17][NH:18][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 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 6364545Methylamine hydrochlorideHCID 151085042-[(tert-Butoxycarbonyl)amino]-2-ethylbutanoic acid

Product 1

HCID 86674754tert-Butyl 3-(methylcarbamoyl)pentan-3-ylcarbamateYield 45%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 2-(tert-butoxycarbonylamino)-2-ethylbutanoic acid (Example 23 a, 400 mg 2 mmol), HBTU (CAN 94790-37-1, 1.3 g, 3 mmol), Et3N (0.7 g, 7 mmol) in DMF (10 mL) was stirred for 30 min, then methanamine hydrochloride (CAN 593-51-1, 260 mg, 6 mmol) was added into the mixture and the solution was stirred overnight. After that, the solution was diluted with water (20 mL) and extracted with ethyl acetate (3×30 mL), the combined organic layer was washed with water (3×50 mL) and brine (60 mL), then evaporated to dryness. The crude product (0.18 g, 45%) obtained as a light yellow solid was used for the next step directly.

Workup

  1. stirringthe solution was stirred overnight
  2. extractionextracted with ethyl acetate (3×30 mL)
  3. washthe combined organic layer was washed with water (3×50 mL) and brine (60 mL)
  4. customevaporated to dryness

Sources & evidence

ORD record
ord-b4cf14b4556f477db8e78c7d1d3ac9d3
Source dataset
uspto-grants-2016_04
Patent number
US09321727B2

Reaction notes

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