HCID 178452692, compound → HCID 178507477, compound

HRID 491815Notes

Reaction equation

HRID 491815 reaction equation
C(OC([NH:8][C:9]1[C:14]2[C:15]([NH:28][C:29]([C@H:31]3[CH2:36][CH2:35][C@H:34]([N:37]4[CH2:41][CH2:40][CH2:39][C:38]4=[O:42])[CH2:33][CH2:32]3)=[O:30])=[C:16]([C:18]([NH:20][C:21]3[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][N:22]=3)=[O:19])[O:17][C:13]=2[CH:12]=[CH:11][CH:10]=1)=O)(C)(C)C>FC(F)(F)C(O)=O>[NH2:8][C:9]1[C:14]2[C:15]([NH:28][C:29]([C@H:31]3[CH2:32][CH2:33][C@H:34]([N:37]4[CH2:41][CH2:40][CH2:39][C:38]4=[O:42])[CH2:35][CH2:36]3)=[O:30])=[C:16]([C:18]([NH:20][C:21]3[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][N:22]=3)=[O:19])[O:17][C:13]=2[CH:12]=[CH:11][CH:10]=1

Participants

3

Reactant 1

HCID 178452692HCID 178452692, compound

Product 1

HCID 178507477HCID 178507477, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

Trans-4-t-butoxycarbonylamino-3-[4-(2-oxopyrrolidin-1-yl)cyclohexylcarbonylamino]-N-(5-chloropyridin-2-yl)benzofuran-2-carboxamide (108 mg) obtained in Example 425 is dissolved in trifluoroacetic acid (2 ml), and the mixture is stirred at room temperature for 2 hours. The reaction solution is concentrated under reduced pressure, and the resulting residue is neutralized with a saturated aqueous sodium hydrogen carbonate solution, and extracted with chloroform. The organic layer is dried over sodium sulfate, and the solvent is evaporated under reduced pressure. The resulting residue is purified by NH-silica gel column chromatography (eluent: n-hexane/ethyl acetate=1/1, then ethyl acetate) to give the title compound (85.4 mg).

Workup

  1. concentrationThe reaction solution is concentrated under reduced pressure
  2. extractionextracted with chloroform
  3. dry with materialThe organic layer is dried over sodium sulfate
  4. customthe solvent is evaporated under reduced pressure
  5. customThe resulting residue is purified by NH-silica gel column chromatography (eluent

Sources & evidence

ORD record
ord-a5d1140bf3d24db6881053cb2425332c
Source dataset
uspto-grants-2009_05
Patent number
US07531537B2

Reaction notes

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