1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → (2S,5R)-5-Allyl-1-((S)-2-methylamino-pent-4-enoyl)-pyrrolidine-2-carboxylic acid phenethyl-amide

HRID 1668423

反応式

HRID 1668423 の反応式
N(CC=C)CC(O)=O.CCN=C=NCCCN(C)C.[CH2:20]([NH:28][C:29]([C@@H:31]1[CH2:35][CH2:34][C@H:33]([CH2:36][CH:37]=[CH2:38])[NH:32]1)=[O:30])[CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.[CH2:39]([N:43]1[CH2:50][CH2:49][CH2:48][C@H:44]1[C:45](N)=[O:46])CC=C>ClCCl.CN(C1C=CN=CC=1)C>[CH2:20]([NH:28][C:29]([C@@H:31]1[CH2:35][CH2:34][C@H:33]([CH2:36][CH:37]=[CH2:38])[N:32]1[C:45](=[O:46])[C@@H:44]([NH:43][CH3:39])[CH2:48][CH:49]=[CH2:50])=[O:30])[CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

参加物

7

反応物 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 76651N-AllylglycineHCID 57612770(2s,5r)-5-Allyl-pyrrolidine-2-carboxylic acid phenethyl-amideHCID 131729076Homoallylproline amide

生成物 1

HCID 66995156(2S,5R)-5-Allyl-1-((S)-2-methylamino-pent-4-enoyl)-pyrrolidine-2-carboxylic acid phenethyl-amide

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 6344Dichloromethane溶媒2 回

実験手順

AllylGlyOH (10.5 g, 26.4 mmol) is suspended in dichloromethane (200 mL) and EDCI (5.1 g, 26.4 mmol) and DMAP (3.2 g, 26.4 mmol) are added to obtain a clear solution. 11E homoallylproline amide in dichloromethane (50 mL) is added and stirred overnight. The product is quenched with saturated bicarb and extracted with dichloromethane, followed by washing with brine, drying over anhydrous magnesium sulfate, filtering and concentrating. The crude is used in following deprotection. LCMS characterization ES+456.1 (m+1).

後処理

  1. customto obtain a clear solution
  2. customThe product is quenched with saturated bicarb
  3. extractionextracted with dichloromethane
  4. washby washing with brine
  5. dry with materialdrying over anhydrous magnesium sulfate
  6. filtrationfiltering
  7. concentrationconcentrating

出典と根拠

ORDレコード
ord-d706b5114cdb4706bd870839d835e45f
出典データセット
uspto-grants-2011_08
特許番号
US07989441B2

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