Methyl iodide → HCID 70090694, compound

HRID 1033858Notes

Reaction equation

HRID 1033858 reaction equation
[CH2:1]([O:8][C:9]([C:11]1[N:12]=[CH:13][O:14][C:15]=1[CH2:16][CH2:17][NH:18][C:19](=[O:48])[C@H:20]([CH2:41][C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1)[NH:21][C@H:22]([C:31]([O:33][CH2:34][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)=[O:32])[CH2:23][CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CI.[C:51](=O)([O-])[O-].[K+].[K+].CN(C)P(=O)(N(C)C)N(C)C>C(OCC)(=O)C>[CH2:1]([O:8][C:9]([C:11]1[N:12]=[CH:13][O:14][C:15]=1[CH2:16][CH2:17][NH:18][C:19](=[O:48])[C@H:20]([CH2:41][C:42]1[CH:43]=[CH:44][CH:45]=[CH:46][CH:47]=1)[N:21]([C@H:22]([C:31]([O:33][CH2:34][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)=[O:32])[CH2:23][CH2:24][C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1)[CH3:51])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 12679HexamethylphosphoramideHCID 15228255HCID 15228255, compound

Product 1

HCID 70090694HCID 70090694, compoundYield 68.1%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 2.6 g of the compound obtained in Example 1, 0.4 ml of methyl iodide, 0.83 g of potassium carbonate and 3 ml of hexamethylphosphoric triamide was stirred at room temperature overnight. Then, ethyl acetate was added to the mixture, and the insolubles were removed by filtration. The filtrate was washed and dried, and then the solvent was removed. The residue was purified by silica gel column chromatography (solvent: chloroform:ethyl acetate=95:5) to obtain 1.81 g (Yield: 68%) of 4-benzyloxycarbonyl-5-(2-[N-((1S)-1-benzyloxycarbonyl-3-phenylpropyl)-N-methyl-(L)-phenylalanyl]aminoethyl}oxazole as an oily product.

Workup

  1. customthe insolubles were removed by filtration
  2. washThe filtrate was washed
  3. customdried
  4. customthe solvent was removed
  5. customThe residue was purified by silica gel column chromatography (solvent: chloroform:ethyl acetate=95:5)

Sources & evidence

ORD record
ord-8c37b908854145b09da6f62321447877
Source dataset
uspto-grants-1994_05
Patent number
US05312826

Reaction notes

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