L-Pyroglutamic Acid → HCID 18648590, compound

HRID 467161Notes

Reaction equation

HRID 467161 reaction equation
[NH:1]1[C:5](=[O:6])[CH2:4][CH2:3][C@H:2]1[C:7]([OH:9])=O.[NH:10]1[CH2:16][CH2:15][CH2:14][C@H:11]1[CH2:12][OH:13].C(N(CC)CC)C>C(Cl)Cl>[NH:1]1[C:5](=[O:6])[CH2:4][CH2:3][C@H:2]1[C:7]([N:10]1[CH2:16][CH2:15][CH2:14][C@H:11]1[CH2:12][OH:13])=[O:9]

Participants

5

Reactant 3

HCID 7405L-Pyroglutamic AcidHCID 8471TriethylamineHCID 640091L-Prolinol

Product 1

HCID 18648590HCID 18648590, compoundYield 23.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

L-pyroglutamic acid (100 g, 0.775 mol), L-prolinol (78.3 g, 0.775 mol) and triethylamine (322 ml) are dissolved in methylene chloride (2.5 l), and a solution of DMC (196.5 g, 1.163 mol) in methylene chloride (600 ml) is added dropwise over a period of forty minutes under water-cooling. The mixture is stirred for a further 3 hours at room temperature, and the reaction liquid is filtered to remove insolubles. The filtrate is concentrated to dryness under reduced pressure, and the residue is crystallized from dioxane-ether to give L-pyroglutamyl-L-prolinol (38.4 g, 23.3%).

Workup

  1. temperaturecooling
  2. customthe reaction liquid
  3. filtrationis filtered
  4. customto remove insolubles
  5. concentrationThe filtrate is concentrated to dryness under reduced pressure
  6. customthe residue is crystallized from dioxane-ether

Sources & evidence

ORD record
ord-edf8007e59b94288993e8e502071bb06
Source dataset
uspto-grants-1992_10
Patent number
US05158970

Reaction notes

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