Trifluoroacetic acid → HCID 86751163, compound

HRID 2258031Notes

Reaction equation

HRID 2258031 reaction equation
C(OC([NH:8][CH:9]([CH:14]([C:24]1[CH:29]=[CH:28][CH:27]=[C:26]([O:30][CH3:31])[CH:25]=1)[S:15][C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([O:22][CH3:23])[CH:17]=1)[C:10]([O:12][CH3:13])=[O:11])=O)(C)(C)C.FC(F)(F)C(O)=O>C(Cl)Cl>[NH2:8][CH:9]([CH:14]([C:24]1[CH:29]=[CH:28][CH:27]=[C:26]([O:30][CH3:31])[CH:25]=1)[S:15][C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([O:22][CH3:23])[CH:17]=1)[C:10]([O:12][CH3:13])=[O:11]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86751162HCID 86751162, compound

Product 1

HCID 86751163HCID 86751163, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 0.110 g (0.25 mmol) of (R,S; R,S)-2-tert-butoxycarbonylamino-3-(3-methoxyphenyl)-3-(3-methoxyphenyl-sulfanyl) propionic acid, methyl ester of Example 31 and 0.75 mL of trifluoroacetic acid in 2 mL of methylene chloride is stirred at room temperature for 30 minutes. The solvent is evaporated ant the residue is dissolved in 100 mL of ethyl acetate. The solution is washed with 2×80 mL of 1N sodium hydroxide and 80 mL of brine and then dried (magnesium sulfate) and evaporated to give the product as a mixture of diastereomers which is used in the next step without further purification; wt 0.084 g (94%); tlc (ethyl acetate/silica gel) one spot Rf 0.4;

Workup

  1. customThe solvent is evaporated ant the residue
  2. dissolutionis dissolved in 100 mL of ethyl acetate
  3. washThe solution is washed with 2×80 mL of 1N sodium hydroxide and 80 mL of brine
  4. dry with materialdried (magnesium sulfate)
  5. customevaporated
  6. customto give the product
  7. additionas a mixture of diastereomers which
  8. customis used in the next step without further purification

Sources & evidence

ORD record
ord-7a67a466d6254b8593f624b6af7053d1
Source dataset
uspto-grants-1997_08
Patent number
US05658943

Reaction notes

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