Citric Acid → HCID 69799811, compound

HRID 1061720Notes

Reaction equation

HRID 1061720 reaction equation
C[O:2][C:3]([C:5]1[S:6][C:7]([C:10](=[O:32])[NH:11][CH2:12][CH2:13][N:14]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[C:15]([NH2:24])=[N:16][C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])=[CH:8][CH:9]=1)=[O:4].[Li+].[OH-].C(O)(=O)CC(CC(O)=O)(C(O)=O)O.C1COCC1>C1COCC1.O>[C:25]([N:14]([CH2:13][CH2:12][NH:11][C:10]([C:7]1[S:6][C:5]([C:3]([OH:4])=[O:2])=[CH:9][CH:8]=1)=[O:32])[C:15]([NH2:24])=[N:16][C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])([O:27][C:28]([CH3:29])([CH3:30])[CH3:31])=[O:26]

Participants

6

Reactant 4

HCID 311Citric AcidHCID 3939Lithium HydroxideHCID 8028TetrahydrofuranHCID 69804016HCID 69804016, compound

Product 1

HCID 69799811HCID 69799811, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 21881883Oxolane--water (1/1)Solvent

Procedure

With continued reference to Scheme K, To Compound XXVII: 5-(2-(N,N′-Bis-(BOC)-guanidino)-ethylcarbamoyl)-thiophene-2-carboxylic acid methyl ester (2.2 g, 4.66 mmol) in 50% THF/H2O (50 ml) was added 1.5 eq. of LiOH (294 mg, 6.99 mmol) and the reaction mixture was left to stir at room temperature for 3 hours. 10% citric acid solution was added until acidic pH and THF was evaporated. The aqueous solution was then extracted with CH2Cl2 (3×70 ml). The organic phases were combined and washed with a solution of Brine, dried over MgSO4 and evaporated to give the desired product in 84% yield. 1H NMR (CD3OD, 400 MHz) δ 1.34-1.66 (m, 21H), 3.49-3.67 (m, 4H), 7.61-7.70 (dd, 2H).

Workup

  1. waitthe reaction mixture was left
  2. customwas evaporated
  3. extractionThe aqueous solution was then extracted with CH2Cl2 (3×70 ml)
  4. washwashed with a solution of Brine
  5. dry with materialdried over MgSO4
  6. customevaporated

Sources & evidence

ORD record
ord-bb8a83779bf64b07993b81fd7d6cba4a
Source dataset
uspto-grants-2005_11
Patent number
US06960594B2

Reaction notes

Loading…