Dicyclohexylcarbodiimide → Methyl bis-(3,4-methylenedioxyphenylmethyl)acetyl-(alpha-methyl-D-tryptophan)

HRID 976042노트

반응식

HRID 976042 반응식
[CH2:1]1[O:9][C:8]2[CH:7]=[CH:6][C:5]([CH2:10][CH:11]([CH2:15][C:16]3[CH:21]=[CH:20][C:19]4[O:22][CH2:23][O:24][C:18]=4[CH:17]=3)[C:12](O)=O)=[CH:4][C:3]=2[O:2]1.C1CCC(N=C=NC2CCCCC2)CC1.C1C=CC2N([OH:49])N=NC=2C=1.[CH3:50][NH:51][C@@:52]([CH3:66])([C:63]([OH:65])=[O:64])[CH2:53][C:54]1[C:62]2[C:57](=[CH:58][CH:59]=[CH:60][CH:61]=2)[NH:56][CH:55]=1>CN(C=O)C.CCOC(C)=O>[CH3:12][C:11]([CH2:10][C:5]1[CH:6]=[CH:7][C:8]2[O:9][CH2:1][O:2][C:3]=2[CH:4]=1)([CH2:15][C:16]1[CH:21]=[CH:20][C:19]2[O:22][CH2:23][O:24][C:18]=2[CH:17]=1)[C:50]([NH:51][C@@:52]([CH3:66])([C:63]([OH:65])=[O:64])[CH2:53][C:54]1[C:62]2[C:57](=[CH:58][CH:59]=[CH:60][CH:61]=2)[NH:56][CH:55]=1)=[O:49]

참가 물질

7

반응물 4

HCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 19968575Bis-(3,4-methylenedioxyphenylmethyl)acetic acidHCID 86750506methyl alpha-methyl-D-tryptophan

생성물 1

HCID 86750507Methyl bis-(3,4-methylenedioxyphenylmethyl)acetyl-(alpha-methyl-D-tryptophan)수율 48.8%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

A solution of 1.0 g (3.0 mmol) of bis-(3,4-methylenedioxyphenylmethyl)acetic acid in 20 mL DMF was treated with 0.68 g (3.3 mmol) of DCC and 0.45 g (3.3 mmol) of HOBt. A solution of 0.73 g (3.15 mmol) of methyl α-methyl-D-tryptophan in 20 mL EtOAc was then added and the solution left stirring for 3 days. The mixture was filtered and the solvent removed under reduced pressure. The residue was taken up in EtOAc and washed with 1N HCl, then saturated NaCl. Drying over MgSO4 and removal of the solvent under reduced pressure left the crude product. Chromatography on silica gel, eluting with a gradient of 10% EtOAc in hexane to 50% EtOAc in hexane gave 0.78 g (48.8% yield) of the product as a white foam. The structure was confirmed by NMR spectroscopy.

후처리

  1. waitthe solution left
  2. filtrationThe mixture was filtered
  3. customthe solvent removed under reduced pressure
  4. washwashed with 1N HCl
  5. dry with materialDrying over MgSO4 and removal of the solvent under reduced pressure
  6. waitleft the crude product
  7. washChromatography on silica gel, eluting with a gradient of 10% EtOAc in hexane to 50% EtOAc in hexane

출처 및 근거

ORD 기록
ord-3f4e2abb31fa446cb02fa0fb735f43af
출처 데이터셋
uspto-grants-1997_03
특허 번호
US05610177

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