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

HRID 976042ノート

反応式

HRID 976042 の反応式
[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]

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-3f4e2abb31fa446cb02fa0fb735f43af
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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