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

HRID 976053ノート

反応式

HRID 976053 の反応式
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]

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-9702d1d0a4924757ac1441109fbcf099
出典データセット
uspto-grants-1997_03
特許番号
US05610177

反応ノート

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