Toluene → (2S,5R)-5-Allyl-1-((S)-2-amino-pent-4-enoyl)-pyrrolidine-2-carboxylic acid phenethyl-amide

HRID 1668424Notes

Reaction equation

HRID 1668424 reaction equation
[CH2:1]([NH:9][C:10]([C@@H:12]1[CH2:16][CH2:15][C@H:14]([CH2:17][CH:18]=[CH2:19])[N:13]1[C:20](=[O:27])[C@@H:21]([NH:25]C)[CH2:22][CH:23]=[CH2:24])=[O:11])[CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.FC(F)(F)C(O)=O.C1(C)C=CC=CC=1>ClCCl>[CH2:1]([NH:9][C:10]([C@@H:12]1[CH2:16][CH2:15][C@H:14]([CH2:17][CH:18]=[CH2:19])[N:13]1[C:20](=[O:27])[C@@H:21]([NH2:25])[CH2:22][CH:23]=[CH2:24])=[O:11])[CH2:2][C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 1140TolueneHCID 6422Trifluoroacetic acidHCID 66995156(2S,5R)-5-Allyl-1-((S)-2-methylamino-pent-4-enoyl)-pyrrolidine-2-carboxylic acid phenethyl-amide

Product 1

HCID 57612851(2S,5R)-5-Allyl-1-((S)-2-amino-pent-4-enoyl)-pyrrolidine-2-carboxylic acid phenethyl-amide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Product 11F is reconstituted in dichloromethane (40 mL) and added trifluoroacetic acid (10 mL). Stirring until reaction complete by HPLC. Toluene is added and concentrated to an amber oil. The product is dissolved in dichloromethane and washed with saturated bicarb followed by drying over anhydrous magnesium sulfate, filtering and concentrating to an amber solid. LCMS characterization ES+356.1 (m+1).

Workup

  1. concentrationconcentrated to an amber oil
  2. dissolutionThe product is dissolved in dichloromethane
  3. washwashed with saturated bicarb
  4. dry with materialby drying over anhydrous magnesium sulfate
  5. filtrationfiltering
  6. concentrationconcentrating to an amber solid

Sources & evidence

ORD record
ord-07f0effe535440e691bc7c89f570ef71
Source dataset
uspto-grants-2011_08
Patent number
US07989441B2

Reaction notes

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