Acetic Anhydride → HCID 13002087, compound

HRID 1106180Notes

Reaction equation

HRID 1106180 reaction equation
[NH2:1][C@H:2]([C:8]([NH:10][C:11]1[CH:16]=[CH:15][C:14]([C:17]2[NH:18][C:19](=[O:26])[C:20](=[CH:24][CH:25]=2)[C:21]([OH:23])=[O:22])=[CH:13][CH:12]=1)=[O:9])[CH2:3][CH2:4][C:5](=[O:7])[NH2:6].C(N(CC)CC)C.[C:34](OC(=O)C)(=[O:36])[CH3:35]>CN(C)C=O>[C:34]([NH:1][C@H:2]([C:8]([NH:10][C:11]1[CH:16]=[CH:15][C:14]([C:17]2[NH:18][C:19](=[O:26])[C:20](=[CH:24][CH:25]=2)[C:21]([OH:23])=[O:22])=[CH:13][CH:12]=1)=[O:9])[CH2:3][CH2:4][C:5](=[O:7])[NH2:6])(=[O:36])[CH3:35]

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 54465448HCID 54465448, compound

Product 1

HCID 13002087HCID 13002087, compoundYield 80.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 30.6 g (83 m mol) of 6-[4-(L-glutaminylamino)phenyl]-1,2-dihydro-2-oxonicotinic acid, 56 ml (0.4 mol) of triethylamine, 19 ml (0.2 mol) of acetic anhydride, and 400 ml dimethylformamide is stirred at room temperature for 3 hrs. The reaction solution is evaporated to dryness under reduced pressure and the residue treated with ice and water. The solid is filtered, washed with water, methanol, ether and dried to give 27.6 g of 6-[4-(N-acetyl-L-glutaminylamino)phenyl]-1,2-dihydro-2-oxonicotinic acid; [α]D23 +19° (cl, DMSO). ##EQU45##

Workup

  1. customThe reaction solution is evaporated to dryness under reduced pressure
  2. additionthe residue treated with ice and water
  3. filtrationThe solid is filtered
  4. washwashed with water, methanol, ether
  5. customdried

Sources & evidence

ORD record
ord-f3ae9966895449f7a5d4a8c46e0cfbe7
Source dataset
uspto-grants-1982_01
Patent number
US04311698

Reaction notes

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