Hydrochloric Acid → HCID 86737872, compound

HRID 1277800Notes

Reaction equation

[NH2:1][C@H:2]([C:4]([NH:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]2[NH:14][C:15](=[O:22])[C:16](=[CH:20][CH:21]=2)[C:17]([OH:19])=[O:18])=[CH:9][CH:8]=1)=[O:5])[CH3:3].CN([CH:26]=[O:27])C.C(OC(=O)C)=O.Cl>CCN(CC)CC.O>[CH:26]([NH:1][C@H:2]([C:4]([NH:6][C:7]1[CH:8]=[CH:9][C:10]([C:13]2[NH:14][C:15](=[O:22])[C:16](=[CH:20][CH:21]=2)[C:17]([OH:19])=[O:18])=[CH:11][CH:12]=1)=[O:5])[CH3:3])=[O:27]

Participants

Conditions

Temperature: 5 °C

Procedure

A suspension of 1.0 g (3.3 mM) of 6-[4-(L-alanylamino)phenyl]-1,2-dihydro-2-oxonicotinic acid, Example 4, and 6 ml of DMF was stirred at 5° C. Addition of 1.5 ml of Et3N gave a clear solution. A 3 ml portion of acetic-formic anhydride [Fieser & Fieser "Reagents for Organic Synthesis," Vol. 1, p. 4, 1967] was added and the mixture stirred at 5° C. for 30 minutes. Addition of 0.6 ml Et3N gave a clear solution which was stirred at 5° C. for 40 minutes. Another 2 ml of the anhydride was added and the mixture stirred at room temperature for 2 hours. The reaction mixture was poured into water and the pH adjusted to 8 with Et3N. The pH of the solution was lowered to 3.6 with aqueous HCl and the resulting solids filtered, washed with water and dried, giving 0.86 g of 6-[4-(N-formyl-L-alanylamino)phenyl]-1,2-dihydro-2-oxonicotinic acid; [α]D23 -50° (Cl, 75% DMF-pyridine; ##EQU18##

Workup

customgave a clear solution
stirringthe mixture stirred at 5° C. for 30 minutes
customgave a clear solution which
stirringwas stirred at 5° C. for 40 minutes
stirringthe mixture stirred at room temperature for 2 hours
filtrationthe resulting solids filtered
washwashed with water
customdried

Sources & evidence

ORD record: ord-7ee675d3d50d4d9886c99e8f05adf7c8
Source dataset: uspto-grants-1981_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04278681

Reaction notes

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