L-Pyroglutamic Acid → HCID 76443731, compound

HRID 1982630Notes

Reaction equation

HRID 1982630 reaction equation
[NH2:1][C@@H:2]([CH2:13][CH:14]([CH3:16])[CH3:15])[CH2:3][NH:4][CH2:5][C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7].[NH:17]1[C:21](=[O:22])[CH2:20][CH2:19][C@H:18]1[C:23](O)=[O:24].O.OC1C2N=NNC=2C=CC=1.C1(N=C=NC2CCCCC2)CCCCC1>CN(C)C=O>[CH3:15][CH:14]([CH3:16])[CH2:13][CH:2]([NH:1][C:23]([CH:18]1[CH2:19][CH2:20][C:21](=[O:22])[NH:17]1)=[O:24])[CH2:3][NH:4][CH2:5][C:6]([O:8][C:9]([CH3:10])([CH3:11])[CH3:12])=[O:7]

Participants

6

Reactant 4

HCID 7405L-Pyroglutamic AcidHCID 10868DicyclohexylcarbodiimideHCID 131714758HCID 131714758, compoundHCID 178526939HCID 178526939, compound

Product 1

HCID 76443731HCID 76443731, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A solution of 1.54 g of (S)-N-(2-amino-4-methylpentyl)glycine, 1,1-dimethylethyl ester, 890 mg of L-pyroglutamic acid, and 904 mg of hydroxybenzotriazole, hydrate in 30 ml of N,N-dimethylformamide is cooled in ice and treated dropwise with a solution of 1.4 g of N,N'-dicyclohexylcarbodiimide in 5 ml of N,N-dimethylformamide. After stirring at 0° for 0.5 hours, the mixture is kept at room temperature overnight. The mixture is filtered and the solvent distilled off under high vacuum. The residue is taken up in ethyl acetate and the ethyl acetate washed two times with water. The water is adjusted to pH 6 and lyophilized. The residue is chromatographed on 95 g of silica gel eluting with chloroform/methanol, (94:6). Combining the appropriate fractions gives 1.2 g of [S-(R*,R*)]-N-[4-methyl-2-[[(5-oxo-2-pyrrolidinyl]carbonyl)amino]pentyl]glycine, 1,1-dimethylethyl ester. The product is homogeneous by thin layer chromatography.

Workup

  1. waitthe mixture is kept at room temperature overnight
  2. filtrationThe mixture is filtered
  3. distillationthe solvent distilled off under high vacuum
  4. washthe ethyl acetate washed two times with water
  5. customThe residue is chromatographed on 95 g of silica gel eluting with chloroform/methanol, (94:6)

Sources & evidence

ORD record
ord-7d4a28cc1b824cc99a09bbe3903dd1d5
Source dataset
uspto-grants-1986_06
Patent number
US04596819

Reaction notes

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