Trifluoroacetic acid → HCID 10323749, compound

HRID 431508Notes

Reaction equation

HRID 431508 reaction equation
C([O:5][C:6](=[O:39])[C@@H:7]([NH:28][C:29]([O:31][CH2:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)=[O:30])[CH2:8][NH:9][C:10]([C:12]1[S:13][C:14]([CH2:17][CH2:18][C:19](=[O:27])[NH:20][C:21]2[NH:22][CH2:23][CH2:24][CH2:25][N:26]=2)=[CH:15][CH:16]=1)=[O:11])(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[CH2:32]([O:31][C:29]([NH:28][C@@H:7]([CH2:8][NH:9][C:10]([C:12]1[S:13][C:14]([CH2:17][CH2:18][C:19](=[O:27])[NH:20][C:21]2[NH:22][CH2:23][CH2:24][CH2:25][N:26]=2)=[CH:15][CH:16]=1)=[O:11])[C:6]([OH:39])=[O:5])=[O:30])[C:33]1[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 57199794HCID 57199794, compound

Product 1

HCID 10323749HCID 10323749, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

50 mg of the product obtained in step h) were dissolved in 5 ml of dichloromethane, and with stirring 0.5 ml of trifluoroacetic acid were added dropwise at room temperature. After 4 hours the ester was no more detectable. The mixture was evaporated under reduced pressure, and the remaining residue was dissolved in acetic acid and again evaporated under reduced pressure. This procedure was repeated twice. Then the residue was triturated vigorously with diethyl ether. The crystals formed were isolated by suction followed by washing with diethyl ether. After drying in vacuo 30 mg of the title compound were obtained as a pale yellow powder.

Workup

  1. additionwere added dropwise at room temperature
  2. customThe mixture was evaporated under reduced pressure
  3. dissolutionthe remaining residue was dissolved in acetic acid
  4. customagain evaporated under reduced pressure
  5. customThen the residue was triturated vigorously with diethyl ether
  6. customThe crystals formed
  7. customwere isolated by suction
  8. washby washing with diethyl ether
  9. dry with materialAfter drying in vacuo 30 mg of the title compound
  10. customwere obtained as a pale yellow powder

Sources & evidence

ORD record
ord-1d4fc0d897ba497ab961f4c8af33ca50
Source dataset
uspto-grants-2003_12
Patent number
US06660728B2

Reaction notes

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