N-Acetyl-DL-methionine → HCID 178503723, compound

HRID 1106114Notes

Reaction equation

HRID 1106114 reaction equation
[C:1]([NH:4][CH:5]([C:10]([OH:12])=O)[CH2:6][CH2:7][S:8][CH3:9])(=[O:3])[CH3:2].ClC(OCC(C)C)=O.[NH2:21][C:22]1[CH:27]=[CH:26][C:25]([C:28]2[N:33]=[C:32]([OH:34])[C:31]([C:35]([OH:37])=[O:36])=[CH:30][N:29]=2)=[CH:24][CH:23]=1.CC(N(C)C)=O>C(N(CC)CC)C.ClCCl>[C:1]([NH:4][CH:5]([C:10]([NH:21][C:22]1[CH:23]=[CH:24][C:25]([C:28]2[N:33]=[C:32]([OH:34])[C:31]([C:35]([OH:37])=[O:36])=[CH:30][N:29]=2)=[CH:26][CH:27]=1)=[O:12])[CH2:6][CH2:7][S:8][CH3:9])(=[O:3])[CH3:2]

Participants

7

Reactant 4

HCID 6180N-Acetyl-DL-methionineHCID 31374DimethylacetamideHCID 62365Isobutyl chloroformateHCID 178507442HCID 178507442, compound

Product 1

HCID 178503723HCID 178503723, compoundYield 57.1%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent2×

Procedure

A suspension of 14.34 g (75 mmol) of N-acetyl-DL-methionine and 150 ml of dichloromethane is stirred at -15° and 10.5 ml (75 mmol) of triethylamine is added followed by 9.75 ml (75 mmol) of isobutyl chloroformate. After stirring for 20 minutes at -15° C., a solution of 11.6 g (50 mmol) of 2-(4-aminophenyl)-4-hydroxy-5-pyrimidine carboxylic acid in 200 ml of dimethylacetamide containing 7.7 ml (55 mmol) of triethylamine is added at -15° C. The mixture is stirred at 0° C. for 3 hrs and overnight at room temperature. The mixture is evaporated and the residue triturated with water. The aqueous suspension, after adjusting the pH to 2.5 with dilute HCl is filtered, washed with water, and dried to give 11.54 g of 2-[4-(N-acetyl-DL-methionylamino)phenyl]-4-hydroxy-5-pyrimidine carboxylic acid; mp 259° C. dec.

Workup

  1. stirringAfter stirring for 20 minutes at -15° C.
  2. stirringThe mixture is stirred at 0° C. for 3 hrs and overnight at room temperature
  3. customThe mixture is evaporated
  4. customthe residue triturated with water
  5. filtrationis filtered
  6. washwashed with water
  7. customdried

Sources & evidence

ORD record
ord-05d69929a85042e98f25dfbd14c9cd8c
Source dataset
uspto-grants-1982_01
Patent number
US04311699

Reaction notes

Loading…