Hydrochloric Acid → (3RS)-3-[(2S)-1-(3-(N-benzyl-N-methylcarbamoyl)propanoyl]pyrrolidin-2-yl)-3-hydroxypropionic acid ethyl ester

HRID 248890ノート

反応式

HRID 248890 の反応式
II.Br[CH2:4][C:5]([O:7][CH2:8][CH3:9])=[O:6].[CH2:10]([N:17]([CH3:31])[C:18]([CH2:20][CH2:21][C:22]([N:24]1[CH2:28][CH2:27][CH2:26][C@H:25]1[CH:29]=[O:30])=[O:23])=[O:19])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.Cl>C1COCC1.C1C=CC=CC=1.[Zn]>[CH2:8]([O:7][C:5](=[O:6])[CH2:4][CH:29]([C@@H:25]1[CH2:26][CH2:27][CH2:28][N:24]1[C:22](=[O:23])[CH2:21][CH2:20][C:18](=[O:19])[N:17]([CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[CH3:31])[OH:30])[CH3:9]

参加物

8

反応物 4

HCID 313Hydrochloric AcidHCID 807IodineHCID 7748Ethyl bromoacetateHCID 14674666(2S)-1-[3-(N-benzyl-N-methylcarbamoyl) propanoyl]pyrrolidin-2-al

生成物 1

HCID 15660989(3RS)-3-[(2S)-1-(3-(N-benzyl-N-methylcarbamoyl)propanoyl]pyrrolidin-2-yl)-3-hydroxypropionic acid ethyl ester

試薬・触媒・溶媒 3

HCID 23994Zinc触媒HCID 241Benzene溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

Zinc powder (482 mg) and a small amount of iodine were added to a solution of ethyl bromoacetate (0.70 ml) in THF (6 ml). The mixture was refluxed for 30 mins. The solution was added dropwise to a solution of (2S)-1-[3-(N-benzyl-N-methylcarbamoyl)propanoyl]pyrrolidin -2-al (1.21 g) in benzene (10 ml). The mixture was refluxed for 30 mins. After reaction, 1N hydrochloric acid was added to the mixture. The mixture was extracted with EtOAc. The extract was washed, dried, and evaporated. The residue was purified by column chromatography on silica gel (hexane-EtOAc) to give the title compound (1.21 g) having the following physical data:

後処理

  1. temperatureThe mixture was refluxed for 30 mins
  2. temperatureThe mixture was refluxed for 30 mins
  3. additionwas added to the mixture
  4. extractionThe mixture was extracted with EtOAc
  5. washThe extract was washed
  6. customdried
  7. customevaporated
  8. customThe residue was purified by column chromatography on silica gel (hexane-EtOAc)

出典と根拠

ORDレコード
ord-b02c8cf2a333407eb8ad9ff787dfc7a1
出典データセット
uspto-grants-1993_05
特許番号
US05212191

反応ノート

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