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

반응식

HRID 1668423 반응식
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

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 6344Dichloromethane용매2회

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-d706b5114cdb4706bd870839d835e45f
출처 데이터셋
uspto-grants-2011_08
특허 번호
US07989441B2

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