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

HRID 2286619Notes

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

Conditions

Temperature: -15 °C

Procedure

A suspension of 14.34 g (75 mmol) of N-acetyl-DL-methionine and 150 ml of dichloromethane is stirred at -15° C. 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

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

Sources & evidence

ORD record: ord-1acf05f8b3924432a64056dc8274433b
Source dataset: uspto-grants-1981_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04267180

Reaction notes

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