Citric Acid → HCID 131729357, compound

HRID 419772Notes

Reaction equation

HRID 419772 reaction equation
Br[C:2]1[C:7]2[N:8]=[C:9]([C@:11]3([CH3:26])[CH2:15][CH2:14][CH2:13][N:12]3[C:16]([O:18][CH2:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)=[O:17])[S:10][C:6]=2[CH:5]=[CH:4][CH:3]=1.[Cu][C:28]#[N:29].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>CN(C)C=O.[Cl-].[Na+].O>[C:28]([C:2]1[C:7]2[N:8]=[C:9]([C@:11]3([CH3:26])[CH2:15][CH2:14][CH2:13][N:12]3[C:16]([O:18][CH2:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)=[O:17])[S:10][C:6]=2[CH:5]=[CH:4][CH:3]=1)#[N:29]

Participants

6

Reactant 3

HCID 311Citric AcidHCID 131729358HCID 131729358, compoundHCID 178418546HCID 178418546, compound

Product 1

HCID 131729357HCID 131729357, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

A mixture of EXAMPLE 5D (100 mg) and copper(I) cyanide (35.3 mg) in N,N-dimethylformamide (2.5 mL) was heated in a microwave reactor at 205° C. for 30 minutes. This reaction was repeated twice, and after cooling, the combined three reaction mixtures were treated with 5% aqueous citric acid and brine and extracted with ethyl acetate. The aqueous layer was treated with 5% aqueous potassium sodium tartrate and ethyl acetate. The combined organic layers were washed with aqueous sodium bicarbonate, dried over magnesium sulfate, filtered and concentrated, and the residue purified by flash chromatography using 98:2 dichloromethane/ethyl acetate to afford the title compound.

Workup

  1. temperatureafter cooling
  2. customthree reaction mixtures
  3. extractionextracted with ethyl acetate
  4. additionThe aqueous layer was treated with 5% aqueous potassium sodium tartrate and ethyl acetate
  5. washThe combined organic layers were washed with aqueous sodium bicarbonate
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customthe residue purified by flash chromatography

Sources & evidence

ORD record
ord-08a039ff04d64c28ae32a07cab5c6921
Source dataset
uspto-grants-2012_01
Patent number
US08093396B2

Reaction notes

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