Triethylamine → HCID 70204287, compound

HRID 651817Notes

Reaction equation

HRID 651817 reaction equation
[C:1]([O:5][C:6]([C@H:8]([C@@H:18]([CH2:31][CH:32]([CH3:34])[CH3:33])[C:19]([NH:21][N:22]1[C:27](=[O:28])[NH:26][C:25](=O)N[C:23]1=[O:30])=[O:20])[CH2:9][CH2:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(OC(=O)CN[CH2:41][C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1)C.C(N(CC)CC)C>C1(C)C=CC=CC=1.C(OCC)(=O)C>[CH2:41]([N:26]1[CH2:25][C:23](=[O:30])[N:22]([NH:21][C:19](=[O:20])[C@@H:18]([C@@H:8]([C:6]([O:5][C:1]([CH3:3])([CH3:4])[CH3:2])=[O:7])[CH2:9][CH:10]=[CH:11][C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH2:31][CH:32]([CH3:34])[CH3:33])[C:27]1=[O:28])[C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 80908N-Benzylglycine ethyl esterHCID 70237630HCID 70237630, compound

Product 1

HCID 70204287HCID 70204287, compoundYield 105.7%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 0.772 g of (E)-2(S)-(tert-butoxycarbonyl)-1(R)-isobutyl-5-phenylpent-4-enyl-1,3,4-oxadiazol-2(3H)-one (prepared as described in Example 34, part (i)) in 10 ml of toluene was treated with 0.387 g of N-benzyl glycine ethyl ester and 0.278 ml of triethylamine and heated overnight at reflux temperature. The mixture was cooled then diluted with ethyl acetate and washed in sequence with 5% aqueous citric acid, 5% aqueous sodium hydrogen carbonate and saturated aqueous sodium chloride and then dried over anhydrous magnesium sulphate. Evaporation gave 0.918 g of N-(3-Benzyl-2,5-dioxo-1-imidazolidinyl)-2(R)-[1(S)-(tert-butoxycarbonyl)-4-phenyl-3-butenyl]-4-methylvaleramide in the form of a white foam.

Workup

  1. temperatureheated overnight
  2. temperatureat reflux temperature
  3. temperatureThe mixture was cooled
  4. washwashed in sequence with 5% aqueous citric acid, 5% aqueous sodium hydrogen carbonate and saturated aqueous sodium chloride
  5. dry with materialdried over anhydrous magnesium sulphate
  6. customEvaporation

Sources & evidence

ORD record
ord-1a9ba6e00a8f4a9591f507db9e3dd822
Source dataset
uspto-grants-2001_08
Patent number
US06281363B1

Reaction notes

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