Dicyclohexylcarbodiimide → HCID 11976036, compound

HRID 1782112Notes

Reaction equation

HRID 1782112 reaction equation
C(OC([NH:8][C:9]1[CH:10]=[CH:11][C:12]([O:18]C(C)(C)C)=[C:13]([CH:17]=1)[C:14]([OH:16])=[O:15])=O)(C)(C)C.OC1C2N=NNC=2C=CC=1.C1CCC(N=C=NC2CCCCC2)CC1.O[C:49]1[CH:57]=[CH:56][C:52]([C:53]([NH2:55])=[S:54])=[CH:51][CH:50]=1>CN(C)C=O.C(OCC)(=O)C>[C:53]([C:52]1[CH:56]=[CH:57][C:49]([O:16][C:14](=[O:15])[C:13]2[CH:17]=[C:9]([NH2:8])[CH:10]=[CH:11][C:12]=2[OH:18])=[CH:50][CH:51]=1)(=[S:54])[NH2:55]

Participants

7

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 27593444-HydroxythiobenzamideHCID 66738398HCID 66738398, compoundHCID 178418300HCID 178418300, compound

Product 1

HCID 11976036HCID 11976036, compoundYield 48%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

To the solution of 4- or 5-tert-butoxycarbonylamino-2-hydroxy-benzoic acid (2) (3.0 mmol) in 50 mL of dimethylformamide, hydroxybenzotriazole (3.3 mmol) and DCC (3.3 mmol) were added with stirring at 0° C. for 1 h. To the reaction mixture, 4-hydroxy-thiobenzamide (3.0 mmol) was added and stirred mechanically for 3 h at 0°C. and 72 h at room temperature. After filtration, the filtrate was evaporated under reduced pressure to remove the solvent. The oily residue thus obtained was dissolved in ethyl acetate; the organic layer washed with brine, dried on anhydrous MgSO4, filtered and the solvent evaporated. The crude intermediate (7) was treated with a solution of 40% TFA in CH2Cl2. After 2 h the solvent was removed to obtain compound (8) as a crude residue. The residue was loaded on a silica gel open column and eluted with CH2Cl21MeOH (8/2), from which 4- or 5-Amino-2-hydroxy-benzoic acid 4-thiocarbamoyl-phenyl ester (8), compound of Formula XXVII, was obtained (48% yield).

Workup

  1. stirringstirred mechanically for 3 h at 0°C. and 72 h at room temperature
  2. filtrationAfter filtration
  3. customthe filtrate was evaporated under reduced pressure
  4. customto remove the solvent
  5. customThe oily residue thus obtained
  6. washthe organic layer washed with brine
  7. dry with materialdried on anhydrous MgSO4
  8. filtrationfiltered
  9. customthe solvent evaporated
  10. additionThe crude intermediate (7) was treated with a solution of 40% TFA in CH2Cl2
  11. customAfter 2 h the solvent was removed

Sources & evidence

ORD record
ord-91f794e2c45f4da0aa5f8a5161f797bb
Source dataset
uspto-grants-2009_03
Patent number
US07498355B2

Reaction notes

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