Nalpha-[N-t-Butoxycarbonyl-3-(2-pyridyl)-D-alanyl]-1,beta-dimethyl-D-tryptophan methyl ester → (3R,6R)-3-[(R)-1-(1-methylindol-3-yl)ethyl]-6-(2-pyridylmethyl)piperazine-2,5-dione

HRID 1382248ノート

反応式

HRID 1382248 の反応式
COC(=O)[C@@H:4]([CH:24]([CH3:35])[C:25]1[C:33]2[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=2)[N:27]([CH3:34])[CH:26]=1)[NH:5][C:6](=[O:23])[C@@H:7]([CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][N:18]=1)[NH:8][C:9](OC(C)(C)C)=[O:10]>FC(F)(F)C(O)=O>[CH3:34][N:27]1[C:28]2[C:33](=[CH:32][CH:31]=[CH:30][CH:29]=2)[C:25]([C@H:24]([C@H:4]2[NH:5][C:6](=[O:23])[C@@H:7]([CH2:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][N:18]=3)[NH:8][C:9]2=[O:10])[CH3:35])=[CH:26]1

参加物

3

反応物 1

HCID 22841452Nalpha-[N-t-Butoxycarbonyl-3-(2-pyridyl)-D-alanyl]-1,beta-dimethyl-D-tryptophan methyl ester

生成物 1

HCID 14151964(3R,6R)-3-[(R)-1-(1-methylindol-3-yl)ethyl]-6-(2-pyridylmethyl)piperazine-2,5-dione

試薬・触媒・溶媒 1

HCID 6422Trifluoroacetic acid溶媒

実験手順

A mixture of Nα -[N-t-butoxycarbonyl-3-(2-pyridyl)-D-alanyl]-1,β-dimethyl-D-tryptophan methyl ester (10.54 g) and trifluoroacetic acid (80 ml) was stirred on an ice bath for 30 minutes. After removal of the solvent, resultant crude residue was dissolved in ethanol (150 ml) and saturated ammonia in ethanol (150 ml) was added to the solution and resultant mixture was stirred for 16 hours at ambient temperature. After evaporation of the solvent, chloroform (200 ml) was added to the mixture. The insoluble material was filtered off and again solvent was evaporated in vacuo to give an oil which was chromatographed on silica gel (250 g, chloroform-methanol 20:1 as eluent) to afford (3R,6R)-3-[(R)-1-(1-methylindol-3-yl)ethyl]-6-(2-pyridylmethyl)piperazine-2,5-dione. Crystallization from ethanol yielded 3.14 g of the crystals.

後処理

  1. customAfter removal of the solvent, resultant crude residue
  2. dissolutionwas dissolved in ethanol (150 ml)
  3. additionsaturated ammonia in ethanol (150 ml) was added to the solution and resultant mixture
  4. stirringwas stirred for 16 hours at ambient temperature
  5. customAfter evaporation of the solvent, chloroform (200 ml)
  6. additionwas added to the mixture
  7. filtrationThe insoluble material was filtered off
  8. customagain solvent was evaporated in vacuo
  9. customto give an oil which
  10. customwas chromatographed on silica gel (250 g, chloroform-methanol 20:1 as eluent)

出典と根拠

ORDレコード
ord-6f99e5e9ddc3481786b8388c4a8c04fe
出典データセット
uspto-grants-1989_02
特許番号
US04806538

反応ノート

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