Trifluoroacetic acid → HCID 22337022, compound

HRID 585513Notes

Reaction equation

HRID 585513 reaction equation
C(O)(C(F)(F)F)=O.C([SiH](CC)CC)C.[Cl:15][C:16]1[S:20][C:19]([C:21]([NH:23][C:24]2[CH:32]=[CH:31][CH:30]=[C:29]3[C:25]=2[CH:26](O)[N:27]([CH2:34][C:35]2[CH:36]=[C:37]([CH:47]=[CH:48][CH:49]=2)[CH2:38][NH:39]C(=O)OC(C)(C)C)[C:28]3=[O:33])=[O:22])=[CH:18][CH:17]=1>ClCCl>[NH2:39][CH2:38][C:37]1[CH:36]=[C:35]([CH:49]=[CH:48][CH:47]=1)[CH2:34][N:27]1[CH2:26][C:25]2[C:29](=[CH:30][CH:31]=[CH:32][C:24]=2[NH:23][C:21]([C:19]2[S:20][C:16]([Cl:15])=[CH:17][CH:18]=2)=[O:22])[C:28]1=[O:33]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 22337077HCID 22337077, compound

Product 1

HCID 22337022HCID 22337022, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

0.21 ml (2.7 mmol) of TFA and 0.07 ml (0.45 mmol) of triethylsilane are added dropwise to a solution of 181 mg (purity 66%, 0.22 mmol) of tert-butyl 3-[(4-{[(5-chloro-2-thienyl)carbonyl]amino}-3-hydroxy-1-oxo-1,3-dihydro-2H-isoindol-2-yl)methyl]benzylcarbamate in 4.5 ml of dichloromethane. The solution is stirred at room temperature overnight and then concentrated and dried under high vaccum. The residue is taken up in dichloromethane/methanol and the mixture is washed with 1N sodium hydroxide solution, dried over magnesium sulfate and concentrated. Ether is added to the residue, the mixture is filtered off with suction and the product is dried under high vacuum. Yield: 84 mg (90.7% of theory); MS (DCI, NH3): m/z (%)=412 (M+H, 100); HPLC (Method 2): rt (%)=6.25 (80).

Workup

  1. concentrationconcentrated
  2. customdried under high vaccum
  3. washthe mixture is washed with 1N sodium hydroxide solution
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated
  6. additionEther is added to the residue
  7. filtrationthe mixture is filtered off with suction
  8. customthe product is dried under high vacuum
  9. customrt (%)=6.25 (80)

Sources & evidence

ORD record
ord-34d71f8964be4c52889f2589fd499c1a
Source dataset
uspto-grants-2005_08
Patent number
US06933295B2

Reaction notes

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