Trifluoroacetic acid → HCID 10391325, compound

HRID 230814Notes

Reaction equation

HRID 230814 reaction equation
[CH3:1][C:2]([CH3:42])([CH3:41])[C:3](=[O:40])[CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]([C:17]2[CH:37]=[CH:36][C:20]([CH2:21][N:22]([CH2:30][CH2:31][S:32]([CH3:35])(=[O:34])=[O:33])C(=O)OC(C)(C)C)=[C:19]([CH3:38])[CH:18]=2)([CH2:15][CH3:16])[CH2:13][CH3:14])=[CH:8][C:7]=1[CH3:39].C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH2:13]([C:12]([C:9]1[CH:10]=[CH:11][C:6]([O:5][CH2:4][C:3](=[O:40])[C:2]([CH3:1])([CH3:42])[CH3:41])=[C:7]([CH3:39])[CH:8]=1)([C:17]1[CH:37]=[CH:36][C:20]([CH2:21][NH:22][CH2:30][CH2:31][S:32]([CH3:35])(=[O:34])=[O:33])=[C:19]([CH3:38])[CH:18]=1)[CH2:15][CH3:16])[CH3:14]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 57763466HCID 57763466, compound

Product 1

HCID 10391325HCID 10391325, compoundYield 95.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of t-butyl (4-{1-[4-(3,3-dimethyl-2-oxobutoxy)-3-methylphenyl]-1-ethylpropyl}-2-methylbenzyl)-(2-methanesulfonylethyl)carbamate (0.25, g, 0.41 mmol) and CH2Cl2 (5 mL) is added TFA (5 mL,), stirred for 10 m, and concentrated. The residue is diluted with EtOAc (100 mL), washed with sat.d NaHCO3 (2×30 mL); MgSO4 dried, and chromatographed (90% EtOAc) to give the title compound (0.19 g, 0.39 mmol, 95%).

Workup

  1. concentrationconcentrated
  2. additionThe residue is diluted with EtOAc (100 mL)
  3. washwashed with sat.d NaHCO3 (2×30 mL)
  4. dry with materialMgSO4 dried
  5. customchromatographed (90% EtOAc)

Sources & evidence

ORD record
ord-19d1f2695dcd4b7095847d062c25de87
Source dataset
uspto-grants-2009_07
Patent number
US07566803B2

Reaction notes

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