Citric Acid → HCID 58670131, compound

HRID 2249502Notes

Reaction equation

HRID 2249502 reaction equation
[C:1]([O:5][C:6]([NH:8][C:9]1[C:10]([CH2:21][CH:22]([N:28]=C(C2C=CC=CC=2)C2C=CC=CC=2)[C:23]([O:25][CH2:26][CH3:27])=[O:24])=[N:11][C:12]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[CH:13][CH:14]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>C1COCC1.O>[NH2:28][CH:22]([CH2:21][C:10]1[C:9]([NH:8][C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])=[CH:14][CH:13]=[C:12]([C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)[N:11]=1)[C:23]([O:25][CH2:26][CH3:27])=[O:24]

Participants

5

Reactant 2

HCID 311Citric AcidHCID 58670122HCID 58670122, compound

Product 1

HCID 58670131HCID 58670131, compoundYield 84.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 1J (2.1 g, 3.82 mmol) in THF (30 mL) and H2O (30 mL) at RT was added citric acid (5 g). The reaction was stirred at RT for 1 h. After this time, no starting material was detected by LC-MS. The reaction mixture was extracted with Et2O (3×90 mL). The organic layers were combined and washed with 0.5 N citric acid (2×60 mL). The combined aqueous layers were basified to pH 8 by using 1 N NaOH (dropwise), and then extracted with Et2O (3×90 mL). The combined Et2O extracts were dried (Na2SO4), filtered and concentrated to give the title compound as a oil (1.24 g, 84%). LC/MS (method A): retention time=2.94 min, (M+H)+=386.

Workup

  1. extractionThe reaction mixture was extracted with Et2O (3×90 mL)
  2. washwashed with 0.5 N citric acid (2×60 mL)
  3. extractionthen extracted with Et2O (3×90 mL)
  4. dry with materialThe combined Et2O extracts were dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-ac9ea3ec464f44269c13349ab3678f75
Source dataset
uspto-grants-2008_01
Patent number
US07314882B2

Reaction notes

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