N-Methylbenzeneethanamine → [2-Methyl-1-(methyl-phenethyl-carbamoyl)-propyl]-carbamic acid tert-butyl ester

HRID 491914Notes

Reaction equation

HRID 491914 reaction equation
[CH3:1][NH:2][CH2:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.[C:11]([O:15][C:16]([NH:18][CH:19]([CH:23]([CH3:25])[CH3:24])[C:20]([OH:22])=O)=[O:17])([CH3:14])([CH3:13])[CH3:12].CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C.C(=O)(O)[O-].[Na+]>CN(C=O)C>[C:11]([O:15][C:16](=[O:17])[NH:18][CH:19]([C:20](=[O:22])[N:2]([CH3:1])[CH2:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)[CH:23]([CH3:25])[CH3:24])([CH3:12])([CH3:13])[CH3:14]

Participants

7

Reactant 5

HCID 11503N-MethylbenzeneethanamineHCID 81531DiisopropylethylamineHCID 270655Boc-DL-valineHCID 516892Sodium BicarbonateHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

Product 1

HCID 67023731[2-Methyl-1-(methyl-phenethyl-carbamoyl)-propyl]-carbamic acid tert-butyl ester

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of N-methyl-phenethyl-amine (2.2 mL, 15.3 mmol), 2-tert-butoxycarbonylamino-3-methyl-butyric acid (3.33 g, 15.3 mmol), HBTU (8.7 g, 22.95 mmol), DIPEA (6.1 mL, 33.7 mmol) and DMF (75 mL) was stirred at room temperature for 14 hours. To the resulting mixture was added sodium bicarbonate (400 mL) and the desired product was extracted with ethyl acetate (400 mL×2). The combined organic layers were washed with water, dried over MgSO4 and concentrated under reduced pressure to yield an oil. The oil was purified by column chromatography (50% EtOAc/heptane) to yield a residue.

Workup

  1. extractionthe desired product was extracted with ethyl acetate (400 mL×2)
  2. washThe combined organic layers were washed with water
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated under reduced pressure
  5. customto yield an oil
  6. customThe oil was purified by column chromatography (50% EtOAc/heptane)
  7. customto yield a residue

Sources & evidence

ORD record
ord-7c10d7dd65f843d0b5754a6184febf7c
Source dataset
uspto-grants-2009_05
Patent number
US07531545B2

Reaction notes

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