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Pyridine → (2S)-2-(Phenoxyacetyl)-1-[N-(phenoxyacetyl)-L-prolyl]pyrrolidine

HRID 1720531
ノート
印刷プレビュー

反応式

HRID 1720531 の反応式
[OH:1][CH:2]([C@@H:11]1[CH2:15][CH2:14][CH2:13][N:12]1[C:16](=[O:32])[C@@H:17]1[CH2:21][CH2:20][CH2:19][N:18]1[C:22](=[O:31])[CH2:23][O:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[CH2:3][O:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.N1C=CC=CC=1.FC(F)(F)C(O)=O.C1CCC(N=C=NC2CCCCC2)CC1>CS(C)=O.C1C=CC=CC=1>[O:4]([CH2:3][C:2]([C@@H:11]1[CH2:15][CH2:14][CH2:13][N:12]1[C:16](=[O:32])[C@@H:17]1[CH2:21][CH2:20][CH2:19][N:18]1[C:22](=[O:31])[CH2:23][O:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)=[O:1])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 1049PyridineHCID 6422Trifluoroacetic acidHCID 10868DicyclohexylcarbodiimideHCID 67771420(2S)-2-(1-Hydroxy-2-phenoxyethyl)-1-[N-(phenoxyacetyl)-L-prolyl]pyrrolidin

生成物 1

HCID 67771029(2S)-2-(Phenoxyacetyl)-1-[N-(phenoxyacetyl)-L-prolyl]pyrrolidine収率 76.4%

試薬・触媒・溶媒 2

HCID 241
Benzene
溶媒
HCID 679Dimethyl Sulfoxide溶媒

実験手順

(2S)-2-(1-Hydroxy-2-phenoxyethyl)-1-[N-(phenoxyacetyl)-L-prolyl]pyrrolidine (998 mg) was dissolved in a mixture of DMSO (6 ml) and benzene (3 ml), and thereto were added pyridine (0.18 ml) and trifluoroacetic acid (0.09 ml). After ice-cooling the mixture, DCC (941 mg) was added thereto, and the mixture was stirred at room temperature for 2.5 hours. The precipitated dicyclohexylurea was filtered off, and the filtrate was poured into ice-cold 1N hydrochloric acid, followed by extraction with ethyl acetate. The organic layer was washed with saturated aqueous sodium bicarbonate and saturated brine successively, dried over anhydrous magnesium sulfate, and concentrated. The residue was purified by silica gel column chromatography (eluate: chloroform-methanol) to give 759 mg of the title compound.

後処理

  1. additionwas added
  2. filtrationThe precipitated dicyclohexylurea was filtered off
  3. additionthe filtrate was poured into ice-cold 1N hydrochloric acid
  4. extractionfollowed by extraction with ethyl acetate
  5. washThe organic layer was washed with saturated aqueous sodium bicarbonate and saturated brine successively
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated
  8. customThe residue was purified by silica gel column chromatography (eluate: chloroform-methanol)

出典と根拠

ORDレコード
ord-ab0abd58a2c848b9ace7dbc3dd2f791e
出典データセット
uspto-grants-1996_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05506256

反応ノート

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