Pyridine → 6-[4-[N-acetyl-4-(acetyloxy)-L-prolylamino]phenyl]-1,2-dihydro-2-oxonicotinic acid

HRID 1106189Notes

Reaction equation

HRID 1106189 reaction equation
[C:1]([N:4]1[CH2:27][CH:26]([OH:28])[CH2:25][C@H:5]1[C:6]([NH:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[NH:16][C:17](=[O:24])[C:18](=[CH:22][CH:23]=2)[C:19]([OH:21])=[O:20])=[CH:11][CH:10]=1)=[O:7])(=[O:3])[CH3:2].N1C=CC=CC=1.[C:35](OC(=O)C)(=[O:37])[CH3:36]>CO>[C:1]([N:4]1[CH2:27][CH:26]([O:28][C:35](=[O:37])[CH3:36])[CH2:25][C@H:5]1[C:6]([NH:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[NH:16][C:17](=[O:24])[C:18](=[CH:22][CH:23]=2)[C:19]([OH:21])=[O:20])=[CH:11][CH:10]=1)=[O:7])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 130021066-[4-(N-acetyl-4-hydroxy-L-prolylamino)phenyl]-1,2-dihydro-2-oxonicotinic acid

Product 1

HCID 130021086-[4-[N-acetyl-4-(acetyloxy)-L-prolylamino]phenyl]-1,2-dihydro-2-oxonicotinic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 29.9 g (0.078 mol) of the above pyridone acid, 120 ml of pyridine, and 60 ml of acetic anhydride is stirred overnight at room temperature. The solution is cooled and upon adding methanol, a precipitate forms. The mixture is cooled and then filtered and the solid is air dried. The solid is recrystallized from 1800 ml of 20% water in methanol and dried at 50° under vacuum to give 21.1 g of 6-[4-[N-acetyl-4-(acetyloxy)-L-prolylamino]phenyl]-1,2-dihydro-2-oxonicotinic acid; [α]D23 +17.3° (cl, 75% DMF/pyridine).

Workup

  1. temperatureThe solution is cooled
  2. temperatureThe mixture is cooled
  3. filtrationfiltered
  4. customdried
  5. customThe solid is recrystallized from 1800 ml of 20% water in methanol
  6. customdried at 50° under vacuum

Sources & evidence

ORD record
ord-3d483a8947f944bcb02188e70e01b6c9
Source dataset
uspto-grants-1982_01
Patent number
US04311698

Reaction notes

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