Triethylamine → Methyl bis-(cyclohexylmethyl)acetyl-(alpha-methyl-D-tryptophan)

HRID 976053Notes

Reaction equation

HRID 976053 reaction equation
C[NH:2][C@@:3]([CH3:17])([C:14]([OH:16])=[O:15])[CH2:4][C:5]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[NH:7][CH:6]=1.[CH:18]1([CH2:24][CH:25]([CH2:29][CH:30]2[CH2:35][CH2:34][CH2:33][CH2:32][CH2:31]2)[C:26](Cl)=[O:27])[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]1.[CH3:36]CN(CC)CC>C1COCC1.CCOC(C)=O>[CH3:36][C:25]([CH2:29][CH:30]1[CH2:35][CH2:34][CH2:33][CH2:32][CH2:31]1)([CH2:24][CH:18]1[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]1)[C:26]([NH:2][C@@:3]([CH3:17])([C:14]([OH:16])=[O:15])[CH2:4][C:5]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[NH:7][CH:6]=1)=[O:27]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 19968572Bis-(cyclohexylmethyl)acetyl chlorideHCID 86750506methyl alpha-methyl-D-tryptophan

Product 1

HCID 86750509Methyl bis-(cyclohexylmethyl)acetyl-(alpha-methyl-D-tryptophan)Yield 65%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 0.69 g (3.0 mmol) of methyl α-methyl-D-tryptophan in 20 mL THF was added 0.8 g (3.0 mmol) of bis-(cyclohexylmethyl)acetyl chloride followed by 0.5 mL of Et3N and the suspension stirred at room temperature for 3 days. The mixture was diluted with EtOAc and washed with 1N citric acid, H2O, and saturated NaCl. Drying over MgSO4 and removal of the solvent under reduced pressure left 1.4 g of the crude product as a foam. Chromatography on silica gel, eluting with CHCl3 /EtOAc (95/5) gave 0.91 g (65% yield) of the product as a white foam. The structure was confirmed by NMR and mass spectroscopy.

Workup

  1. washwashed with 1N citric acid, H2O, and saturated NaCl
  2. dry with materialDrying over MgSO4 and removal of the solvent under reduced pressure
  3. waitleft 1.4 g of the crude product as a foam
  4. washChromatography on silica gel, eluting with CHCl3 /EtOAc (95/5)

Sources & evidence

ORD record
ord-9702d1d0a4924757ac1441109fbcf099
Source dataset
uspto-grants-1997_03
Patent number
US05610177

Reaction notes

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