Dimethylformamide → HCID 131714762, compound

HRID 1982653Notes

Reaction equation

HRID 1982653 reaction equation
[NH:1]1[C:5](=[O:6])[CH2:4][CH2:3][C@H:2]1[C:7](O)=O.O.[OH:11][C:12]1[C:20]2N=N[NH:17][C:16]=2[CH:15]=[CH:14][CH:13]=1.C([N:23](CC)CC)C.[CH:28]1(N=C=NC2CCCCC2)[CH2:33]CCC[CH2:29]1.CN(C)[CH:45]=[O:46]>>[NH2:23][C:12](=[O:11])[CH2:13][CH:14]=[CH:15][CH:16]([NH:17][C:45]([CH2:7][CH:2]1[CH2:3][CH2:4][C:5](=[O:6])[NH:1]1)=[O:46])[CH2:20][CH:28]([CH3:33])[CH3:29]

Participants

6

Reactant 5

HCID 6228Dimethylformamide2×HCID 7405L-Pyroglutamic AcidHCID 8471TriethylamineHCID 10868DicyclohexylcarbodiimideHCID 178526939HCID 178526939, compound

Product 1

HCID 131714762HCID 131714762, compound

Procedure

To a suspension of 2.1 g of [S-(E)]-5-amino-7-methyl-3-octenamide, monohydrochloride (prepared in Example 97) in 40 ml of N,N-dimethylformamide is added 1.32 of L-pyroglutamic acid, and 1.38 g of hydroxybenzotriazole hydrate. The mixture is cooled in ice and treated with 1.42 ml of triethylamine followed by a solution of 2.1 g of dicyclohexylcarbodiimide in 10 ml of N,N-dimethylformamide. The solution is kept at 0° for one hour, then at room temperature overnight. After filtering to remove dicyclohexylurea, the solvent is removed under high vacuum. The residue is taken up in chloroform and washed twice with water. On cooling the water extracts, hydroxybenzotriazole precipitates and is removed by filtration. The filtrate in lyophilized. The residue is chromatographed on silica gel, eluting with chloroform/methanol (85/15). Combining the appropriate fractions and recrystallizing the residue from acetonitrile gives 1.03 g of [S-(R*,R*-E)]-N-[5-amino-1-(2-methylpropyl)-5-oxo-2-pentenyl]-5-oxo-2-pyrrolidinecarboxyamide, mp 150°-152°, [α]D23 -39.1° (c 1.19, methanol).

Workup

  1. temperatureThe mixture is cooled in ice
  2. customat room temperature
  3. customovernight
  4. filtrationAfter filtering
  5. customto remove dicyclohexylurea
  6. customthe solvent is removed under high vacuum
  7. washwashed twice with water
  8. temperatureOn cooling the water
  9. customhydroxybenzotriazole precipitates
  10. customis removed by filtration
  11. customThe residue is chromatographed on silica gel
  12. washeluting with chloroform/methanol (85/15)
  13. customrecrystallizing the residue from acetonitrile

Sources & evidence

ORD record
ord-58cb032531e9461d8a0f618672711892
Source dataset
uspto-grants-1986_06
Patent number
US04596819

Reaction notes

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