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

HRID 976053노트

반응식

HRID 976053 반응식
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]

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-9702d1d0a4924757ac1441109fbcf099
출처 데이터셋
uspto-grants-1997_03
특허 번호
US05610177

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