Pyrrolidone carboxylic acid → HCID 178516113, compound

HRID 1106118Notes

Reaction equation

HRID 1106118 reaction equation
[O:1]=[C:2]1[NH:6][CH: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][CH: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 4

HCID 499Pyrrolidone carboxylic acidHCID 8471TriethylamineHCID 24386Thionyl ChlorideHCID 178507442HCID 178507442, compound

Product 1

HCID 178516113HCID 178516113, compoundYield 72.2%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 6344DichloromethaneSolvent

Procedure

A suspension of 3.87 g (30 mmol) of 5-oxo-DL-proline, 2.3 ml (30 mmol) of dimethylformamide, and 50 ml of dichloromethane is stirred at 0°-5° C. and 2.2 ml (30 mmol) of thionyl chloride is added. Stirring is continued at 0°-5° C. for 1.67 hrs and a solution of 4.62 g (20 mmol) of 2-(4-aminophenyl)-4-hydroxy-5-pyrimidine carboxylic acid, 3.1 ml (22 mmol) of triethylamine and 60 ml of dimethylformamide is added. The reaction mixture is stirred at 0°-5° C. for 3 hrs and at room temperature overnight. The solid is filtered, washed with dichloromethane, methanol, and ether, and dried to give 4.94 g of 2-[4-((5-oxo-DL-prolyl)-amino)phenyl]-4-hydroxy-5-pyrimidine carboxylic acid.

Workup

  1. stirringStirring
  2. stirringThe reaction mixture is stirred at 0°-5° C. for 3 hrs and at room temperature overnight
  3. filtrationThe solid is filtered
  4. washwashed with dichloromethane, methanol, and ether
  5. customdried

Sources & evidence

ORD record
ord-9bd281c5d7b74d999c0a7ab0e877c11e
Source dataset
uspto-grants-1982_01
Patent number
US04311699

Reaction notes

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