Anisole → HCID 86745935, compound

HRID 893296Notes

Reaction equation

HRID 893296 reaction equation
[F:1][C:2]([F:43])([F:42])[C:3]1[C:4]([S:32]CC2C=CC(OC)=CC=2)=[C:5]([C:9]([CH2:28][CH:29]([CH3:31])[CH3:30])([CH3:27])[C:10]([NH:12][C@H:13]([C:23]([NH:25][CH3:26])=[O:24])[CH2:14][C:15]2[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=2)=[O:11])[CH:6]=[CH:7][CH:8]=1.C1(OC)C=CC=CC=1>FC(F)(F)C(O)=O>[F:42][C:2]([F:1])([F:43])[C:3]1[C:4]([SH:32])=[C:5]([C:9]([CH2:28][CH:29]([CH3:31])[CH3:30])([CH3:27])[C:10]([NH:12][C@H:13]([C:23]([NH:25][CH3:26])=[O:24])[CH2:14][C:15]2[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=2)=[O:11])[CH:6]=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 7519AnisoleHCID 86745936HCID 86745936, compound

Product 1

HCID 86745935HCID 86745935, compound

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

An ice-cooled solution of 3-trifluoromethyl-2-(4-methoxybenzylthio)-N-[2-(4-methoxyphenyl)-1-(S)-(methylaminocarbonyl)ethyl]-α-(2-methylpropyl)phenylpropanamide (D13) (308 mg, 0.5 mmol) and anisole (0.1 ml) in trifluoroacetic acid (5 ml) was treated with mercuric acetate (160 mg, 0.5 mmol). After 15 min the solvent was evaporated and the residue was azeotroped dry with toluene. The residual oil was triturated with ether to give a white solid, which was separated and washed with a little ether. The solid was dissolved in dry DMF (3 ml) and the solution was purged with nitrogen. Hydrogen sulphide gas was bubbled through the solution for 3 min. The resulting black suspension was purged with nitrogen for 30 min, then the solvent was evaporated in vacuo. Column chromatography (10 g silica) eluting with ethyl acetate and trituration of the product with pentane gave the title compound as a 1:1 mixture of diastereoisomers (88 mg, 35%), mp 88°-102° C.

Workup

  1. customAfter 15 min the solvent was evaporated
  2. customthe residue was azeotroped
  3. dry with materialdry with toluene
  4. customThe residual oil was triturated with ether
  5. customto give a white solid, which
  6. customwas separated
  7. washwashed with a little ether
  8. dissolutionThe solid was dissolved in dry DMF (3 ml)
  9. customthe solution was purged with nitrogen
  10. customHydrogen sulphide gas was bubbled through the solution for 3 min
  11. customThe resulting black suspension was purged with nitrogen for 30 min
  12. customthe solvent was evaporated in vacuo
  13. washColumn chromatography (10 g silica) eluting with ethyl acetate and trituration of the product with pentane

Sources & evidence

ORD record
ord-01f7a05561c54dcdb0821d8ef96bb469
Source dataset
uspto-grants-1992_06
Patent number
US05124322

Reaction notes

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