1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → (2s,5r)-5-Allyl-1-[(s)-2-((s)-2-dimethylamino-propionylamino)-pent-4-enoyl]-pyrrolidine-2-carboxylic acid phenethyl-amide

HRID 1668425Notes

Reaction equation

HRID 1668425 reaction equation
[N:1]([C:8](OC(C)(C)C)=O)([CH3:7])[C@H:2]([C:4](O)=[O:5])[CH3:3].CCN=C=NCCCN(C)C.[CH2:26]([NH:34][C:35]([C@@H:37]1[CH2:41][CH2:40][C@H:39]([CH2:42][CH:43]=[CH2:44])[N:38]1[C:45](=[O:51])[C@@H:46]([NH2:50])[CH2:47][CH:48]=[CH2:49])=[O:36])[CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1>ClCCl.CN(C1C=CN=CC=1)C>[CH2:26]([NH:34][C:35]([C@@H:37]1[CH2:41][CH2:40][C@H:39]([CH2:42][CH:43]=[CH2:44])[N:38]1[C:45](=[O:51])[C@@H:46]([NH:50][C:4](=[O:5])[C@@H:2]([N:1]([CH3:8])[CH3:7])[CH3:3])[CH2:47][CH:48]=[CH2:49])=[O:36])[CH2:27][C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=1

Participants

6

Reactant 3

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 7009590(2S)-2-(((tert-butoxy)carbonyl)(methyl)amino)propanoic acidHCID 57612851(2S,5R)-5-Allyl-1-((S)-2-amino-pent-4-enoyl)-pyrrolidine-2-carboxylic acid phenethyl-amide

Product 1

HCID 66994769(2s,5r)-5-Allyl-1-[(s)-2-((s)-2-dimethylamino-propionylamino)-pent-4-enoyl]-pyrrolidine-2-carboxylic acid phenethyl-amide

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

Boc-N-MeAlaOH (5.36 g, 26.4 mmol) is suspended in dichloromethane (200 mL) and EDCI (5.4 g, 28 mmol) and DMAP (3.4 g, 28 mmol) are added to obtain a clear solution. 11G in dichloromethane (50 mL) is added and stirred overnight followed by quenching with saturated bicarb and extracting with dichloromethane then washing with brine, drying over anhydrous magnesium sulfate, filtering and concentrating. LCMS characterization ES+541.2 (m+1).

Workup

  1. customto obtain a clear solution
  2. customby quenching with saturated bicarb
  3. extractionextracting with dichloromethane
  4. washthen washing with brine
  5. dry with materialdrying over anhydrous magnesium sulfate
  6. filtrationfiltering
  7. concentrationconcentrating

Sources & evidence

ORD record
ord-6425ddb72f4c4809a4f758072192fe84
Source dataset
uspto-grants-2011_08
Patent number
US07989441B2

Reaction notes

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