4-Methylmorpholine → HCID 178474779, compound

HRID 2286621Notes

Reaction equation

[C:1]([NH:4][C@H:5]([C:11]([OH:13])=O)[CH2:6][CH2:7][C:8](=[O:10])[NH2:9])(=[O:3])[CH3:2].C(N(CC)CC)C.ClC(OCC(C)C)=O.[NH2:29][C:30]1[CH:35]=[CH:34][C:33]([C:36]2[N:41]=[C:40]([OH:42])[C:39]([C:43]([OH:45])=[O:44])=[CH:38][N:37]=2)=[CH:32][CH:31]=1.CN1CCOCC1>CN(C)C=O>[C:1]([NH:4][CH:5]([C:11]([NH:29][C:30]1[CH:31]=[CH:32][C:33]([C:36]2[N:41]=[C:40]([OH:42])[C:39]([C:43]([OH:45])=[O:44])=[CH:38][N:37]=2)=[CH:34][CH:35]=1)=[O:13])[CH2:6][CH2:7][C:8](=[O:10])[NH2:9])(=[O:3])[CH3:2]

Participants

Conditions

Temperature: 5 °C

Procedure

A solution of 14.1 g (75mmol) of N-acetyl-L-glutamine and 9.75 ml (75 mmol) of triethylamine in 150 ml of dimethylformamide is stirred at -15° to -20° C. and 9.75 ml (75 mmol) of isobutyl chloroformate is added. After stirring at -15° to -20° C. for 30 min a cold solution of 11.6 g (50 mmol) of 2-(4-aminophenyl)-4-hydroxy-5-pyrimidine carboxylic acid and 7.15 ml (50 mmol) of N-methylmorpholine in 200 ml of dimethylformamide is added at -15° C. The reaction mixture is stirred at -15° C. for 20 min at 5° C. for 3 hrs, and at room temperature overnight. The reaction mixture is evaporated and the residue treated with water. The pH is lowered to 2.5 with hydrochloric acid and the solid is filtered, washed with water, and dried to afford 17.3 g of 2-[4-(N-acetyl-DL-glutaminylamino)phenyl]-4-hydroxy-5-pyrimidine carboxylic acid; mp 247°-248° C. dec. [α]D25 -2.8 (c0.7, DMSO).

Workup

additionis added at -15° C
customat room temperature
customovernight
customThe reaction mixture is evaporated
additionthe residue treated with water
filtrationthe solid is filtered
washwashed with water
customdried

Sources & evidence

ORD record: ord-e0ec169cc2994278b4ffcf9e68010d7f
Source dataset: uspto-grants-1981_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04267180

Reaction notes

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