4-Methylmorpholine → HCID 178474779, compound

HRID 1106116Notes

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.C(OC(Cl)=O)C(C)C.[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 (75 mmol) 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 isobutylchloroformate 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 mml) of N-methylmorpholine in 200 ml of dimethylformamide is added at -15° C. The reaction mixture is stirred at -15° 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]23D -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-3582722e0c73412ca77c0a1d2352e0ac
Source dataset: uspto-grants-1982_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04311699

Reaction notes

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