Trifluoroacetic acid → HCID 67236651, compound

HRID 1521694Notes

Reaction equation

HRID 1521694 reaction equation
COC([C:5]1[N:9]([C:10]([CH3:29])([CH2:12][CH2:13][N:14](C(OC(C)(C)C)=O)[C:15]([O:17]C(C)(C)C)=O)[CH3:11])[C:8]2[CH:30]=[C:31]([C:34]([O:36][CH2:37][C:38]3[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=3)=[O:35])[CH:32]=[CH:33][C:7]=2[N:6]=1)=O.C(O)(C(F)(F)F)=O.C(N(CC)CC)C>C(Cl)Cl>[CH3:11][C:10]1([CH3:29])[N:9]2[C:5](=[N:6][C:7]3[CH:33]=[CH:32][C:31]([C:34]([O:36][CH2:37][C:38]4[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=4)=[O:35])=[CH:30][C:8]=32)[C:15](=[O:17])[NH:14][CH2:13][CH2:12]1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 8471TriethylamineHCID 89595080HCID 89595080, compound

Product 1

HCID 67236651HCID 67236651, compoundYield 46.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of crude 1-({4-[bis(tert-butoxycarbonyl)amino]-2-methylbutan-2-yl}-1H-benzimidazole-2,6-dicarboxylic acid 6-benzyl ester 2-methyl ester (289 mg, 0.47 mmol) in CH2Cl2 (5 mL) is added TFA (1 mL). After 1 h the solvent is evaporated, and CH2Cl2 is added and evaporated from the residue three times to remove excess TFA. The residue is dissolved in methanol (10 mL) and triethylamine (0.72 mL, 5.16 mmol) added. The solution is stirred at room temperature for 16 h. The solvent is evaporated and the residue partitioned between H2O and EtOAc. The organic layer is dried (MgSO4) and purified by flash chromatography, eluting with CH2Cl2/methanol to afford the title compound (80 mg, 44%).

Workup

  1. customAfter 1 h the solvent is evaporated
  2. additionCH2Cl2 is added
  3. customevaporated from the residue three times
  4. customto remove excess TFA
  5. dissolutionThe residue is dissolved in methanol (10 mL)
  6. customThe solvent is evaporated
  7. customthe residue partitioned between H2O and EtOAc
  8. dry with materialThe organic layer is dried (MgSO4)
  9. custompurified by flash chromatography
  10. washeluting with CH2Cl2/methanol

Sources & evidence

ORD record
ord-c860636fae1b44cd909fb1b220d82408
Source dataset
uspto-grants-2015_07
Patent number
US09073926B2

Reaction notes

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