4-Aminosalicylic Acid → HCID 86748782, compound

HRID 1721469Notes

Reaction equation

HRID 1721469 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([OH:11])[C:5](=[CH:9][CH:10]=1)[C:6]([OH:8])=[O:7].O[N:13]1[C:17](=[O:18])[CH2:16][CH2:15][C:14]1=[O:19].C1CCC(N=C=NC2CCCCC2)CC1.[O:35]=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O>O1CCCC1>[OH:35][NH:1][C:2]1[CH:3]=[C:4]([O:11][N:13]2[C:17](=[O:18])[CH2:16][CH2:15][C:14]2=[O:19])[C:5](=[CH:9][CH:10]=1)[C:6]([OH:8])=[O:7]

Participants

6

Reactant 4

HCID 46494-Aminosalicylic AcidHCID 10868DicyclohexylcarbodiimideHCID 14812Phosphorus oxide (P4O10)HCID 80170N-Hydroxysuccinimide

Product 1

HCID 86748782HCID 86748782, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4-Amino salicylic acid (2.07 g, 13 mM), N-hydroxy-succinimide (2.07 g, 18 mmol) and DCC (3.44 g, 19 mmol), which had been dried over night over phosphorus pentoxide in vacuum, were dissolved sequentially in anhy. tetrahydrofuran (150 mL) in a round bottom flask. A vacuum was then applied for 30 seconds, the flask sealed and the reaction allowed to proceed for 7 hours at 1°-0° C., maintaining continuous stirring. After this time, the solvent was removed under vacuum and the residue re-dissolved in 15 mL CHCl3 /acetonitrile (CH3CN) (98:2). This solution was chromatographed using 80 g silica gel, eluting sequentially with 300 mL each, CHCl3 /CH3CN (95:5), CHCl3 /CH3CN (90:10) and CHCl3 /CH3CN (50:50). HASA began eluting in the tail end of CHCl3 /CH3CN (95:5) and continued throughout the elution with 10% CH3CN. A total of 2.4 g (70%) of purified HASA (XXXII) was obtained, Rf =0.64 (CHCl3 /CH3CN, 20.3).

Workup

  1. dissolutionwere dissolved sequentially in anhy
  2. customthe flask sealed
  3. waitto proceed for 7 hours at 1°-0° C.
  4. temperaturemaintaining continuous stirring
  5. customAfter this time, the solvent was removed under vacuum
  6. dissolutionthe residue re-dissolved in 15 mL CHCl3 /acetonitrile (CH3CN) (98:2)
  7. customThis solution was chromatographed
  8. washeluting sequentially with 300 mL each, CHCl3 /CH3CN (95:5), CHCl3 /CH3CN (90:10) and CHCl3 /CH3CN (50:50)
  9. washHASA began eluting in the tail end of CHCl3 /CH3CN (95:5)
  10. washcontinued throughout the elution with 10% CH3CN

Sources & evidence

ORD record
ord-b7a79fe9ff9d419bb98df8ebdb67f4a7
Source dataset
uspto-grants-1996_04
Patent number
US05510500

Reaction notes

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