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

Reaction equation

HRID 1668423 reaction equation
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

Participants

7

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-d706b5114cdb4706bd870839d835e45f
Source dataset
uspto-grants-2011_08
Patent number
US07989441B2

Linked notes

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