Trifluoroacetic acid → HCID 86699363, compound

HRID 333997Notes

Reaction equation

HRID 333997 reaction equation
[OH:1][C@@H:2]([C:28]1[CH:32]=[CH:31][S:30][CH:29]=1)[CH2:3][N:4]([CH2:17][C@H:18]([NH:20]C(=O)OC(C)(C)C)[CH3:19])[S:5]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[N+:14]([O-:16])=[O:15])(=[O:7])=[O:6].FC(F)(F)C(O)=O>ClCCl>[NH2:20][C@H:18]([CH3:19])[CH2:17][N:4]([CH2:3][C@@H:2]([OH:1])[C:28]1[CH:32]=[CH:31][S:30][CH:29]=1)[S:5]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[N+:14]([O-:16])=[O:15])(=[O:6])=[O:7]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86699364HCID 86699364, compound

Product 1

HCID 86699363HCID 86699363, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

602 mg of tert-butyl (R)-1-[N—{(S)-2-hydroxy-2-(thiophen-3-yl)ethyl}-2-nitrophenylsulfonamido]propan-2-ylcarbamate was dissolved in 4 mL of dichloromethane. To the solution, 1 mL of trifluoroacetic acid was added, and the mixture was stirred at room temperature for 1 hour. The reaction solution was concentrated under reduced pressure, and the residue was dissolved in 4 mL of methanol. 1 g of sodium bicarbonate was added thereto, and the mixture was stirred for 1 hour. After filtration, the filtrate was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (dichloromethane:methanol=8:1) to obtain 338 mg of the title compound as a colorless oil (71%).

Workup

  1. concentrationThe reaction solution was concentrated under reduced pressure
  2. dissolutionthe residue was dissolved in 4 mL of methanol
  3. addition1 g of sodium bicarbonate was added
  4. stirringthe mixture was stirred for 1 hour
  5. filtrationAfter filtration
  6. concentrationthe filtrate was concentrated under reduced pressure
  7. customthe residue was purified by silica gel column chromatography (dichloromethane:methanol=8:1)

Sources & evidence

ORD record
ord-110b08948e2547b59c0cf33090bc3b0f
Source dataset
uspto-grants-2014_11
Patent number
US08883792B2

Reaction notes

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