L-Pyroglutamic Acid → HCID 178516172, compound

HRID 2286622Notes

Reaction equation

HRID 2286622 reaction equation
[O:1]=[C:2]1[NH:6][C@H:5]([C:7]([OH:9])=O)[CH2:4][CH2:3]1.S(Cl)(Cl)=O.[NH2:14][C:15]1[CH:20]=[CH:19][C:18]([C:21]2[N:26]=[C:25]([OH:27])[C:24]([C:28]([OH:30])=[O:29])=[CH:23][N:22]=2)=[CH:17][CH:16]=1>C(N(CC)CC)C.CN(C)C=O.ClCCl>[O:1]=[C:2]1[NH:6][C@H:5]([C:7]([NH:14][C:15]2[CH:16]=[CH:17][C:18]([C:21]3[N:26]=[C:25]([OH:27])[C:24]([C:28]([OH:30])=[O:29])=[CH:23][N:22]=3)=[CH:19][CH:20]=2)=[O:9])[CH2:4][CH2:3]1

Participants

7

Reactant 3

HCID 7405L-Pyroglutamic AcidHCID 24386Thionyl ChlorideHCID 178507442HCID 178507442, compound

Product 1

HCID 178516172HCID 178516172, compoundYield 77,708.203%

Reagents, catalysts & solvents 3

HCID 8471TriethylamineCatalystHCID 6228DimethylformamideSolvent2×HCID 6344DichloromethaneSolvent

Procedure

A suspension of 12.9 g (0.1 mol) 5-oxo-L-proline, 7.7 ml (0.1 mol) dimethylformamide, and 150 ml of dichloromethane is stirred at 0°-5° C. and 7.3 ml (0.1 mol) of thionyl chloride is added. The reaction mixture is stirred at 0°-5° C. for 1/2 hrs and at room temperature for 2 hrs. After stirring for 20 minutes at room temperature a solution of 11.55 g (0.05 mmol) of 2-(4-aminophenyl)-4-hydroxy-5-pyrimidine carboxylic acid, 7.7 ml (0.55 mmol) triethylamine, and 150 ml of dimethylformamide is added and stirred at 0°-5° C. for 1 hr and at room temperature overnight. The reaction mixture is filtered and the solid is washed with dichloromethane, methanol, water, methanol, and ether to give 13.3 g of 2-[4-[(5-oxo-L-prolyl)amino]phenyl]-4-hydroxy-5-pyrimidine carboxylic acid; mp>300° C.

Workup

  1. stirringThe reaction mixture is stirred at 0°-5° C. for 1/2 hrs and at room temperature for 2 hrs
  2. additionis added
  3. stirringstirred at 0°-5° C. for 1 hr and at room temperature overnight
  4. filtrationThe reaction mixture is filtered
  5. washthe solid is washed with dichloromethane, methanol, water, methanol, and ether

Sources & evidence

ORD record
ord-032ab164b9bd40c499a3fb1b38717008
Source dataset
uspto-grants-1981_05
Patent number
US04267180

Reaction notes

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