Trifluoroacetic acid → HCID 10048962, compound

HRID 1494130Notes

Reaction equation

HRID 1494130 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][CH2:12][CH2:13][CH2:14][CH2:15][CH:16]([CH2:26][CH2:27][CH2:28][N:29]2[CH:33]=[CH:32][N:31]=[CH:30]2)[CH2:17][CH2:18][C:19]([O:21]C(C)(C)C)=[O:20])(=[O:10])=[O:9])=[CH:4][CH:3]=1.FC(F)(F)C(O)=O>C(Cl)Cl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][CH2:12][CH2:13][CH2:14][CH2:15][CH:16]([CH2:26][CH2:27][CH2:28][N:29]2[CH:33]=[CH:32][N:31]=[CH:30]2)[CH2:17][CH2:18][C:19]([OH:21])=[O:20])(=[O:10])=[O:9])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 14986680HCID 14986680, compound

Product 1

HCID 10048962HCID 10048962, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 0.17 g (0.34 mmol) t-butyl 8-(p-chlorophenylsulfonamido)-4-[3-(1-imidazolyl)propyl]octanoate in 5 mL methylene chloride is added 1 mL trifluoroacetic acid and the solution is stirred at room temperature for 1.5 hours. The solvent is evaporated and the residue taken up in 5 mL water. The pH of the solution is adjusted to 6.5 using 1N aqueous sodium hydroxide. Then the aqueous solution is extracted twice with ethyl acetate. The combined organic layer is washed with water and brine, dried, filtered and concentrated to give a pale yellow oil. The product is triturated five times with 2 mL ether and finally dried to yield 8-(p-chlorophenylsulfonamido)-4-[3-(1-imidazolyl)propyl]octanoic acid, m.p. 136-138° C.

Workup

  1. customThe solvent is evaporated
  2. extractionThen the aqueous solution is extracted twice with ethyl acetate
  3. washThe combined organic layer is washed with water and brine
  4. customdried
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto give a pale yellow oil
  8. customThe product is triturated five times with 2 mL ether
  9. customfinally dried

Sources & evidence

ORD record
ord-026a7f12e1c24303bdfe48a836fe79d9
Source dataset
uspto-grants-1991_06
Patent number
US05025025

Reaction notes

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