Trifluoroacetic acid → HCID 67333637, compound

HRID 1672259Notes

Reaction equation

HRID 1672259 reaction equation
C([O:5][C:6](=[O:40])[CH:7]([NH:17][C:18]([C:20]1[CH:25]=[CH:24][C:23]([C:26]2[CH:31]=[CH:30][C:29]([NH:32][C:33]([C:35]3[O:36][CH:37]=[CH:38][CH:39]=3)=[O:34])=[CH:28][CH:27]=2)=[CH:22][CH:21]=1)=[O:19])[CH2:8][CH2:9][C:10]([O:12]C(C)(C)C)=[O:11])(C)(C)C.C(O)(C(F)(F)F)=O>ClC(Cl)C>[O:36]1[CH:37]=[CH:38][CH:39]=[C:35]1[C:33]([NH:32][C:29]1[CH:28]=[CH:27][C:26]([C:23]2[CH:24]=[CH:25][C:20]([C:18]([NH:17][CH:7]([CH2:8][CH2:9][C:10]([OH:12])=[O:11])[C:6]([OH:40])=[O:5])=[O:19])=[CH:21][CH:22]=2)=[CH:31][CH:30]=1)=[O:34]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67331985HCID 67331985, compound

Product 1

HCID 67333637HCID 67333637, compoundYield 85.6%

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

2-({4′-[(Furan-2-carbonyl)-amino]-biphenyl-4-carbonyl}-amino)-pentanedioic acid di-tert-butyl ester (369 mg, 0.67 mmol) was dissolved in dichloroethane (10 mL) and added to TFA (5 mL) at 0° C. The cooling bath was removed after the addition was complete. The mixture was stirred at room temperature for 3 hrs. and the reaction was complete as determined by TLC. After removing solvent, the residue was washed 3 times with EtOAc. The solid was then dried under vacuum to give 2-({4′-[(Furan-2-carbonyl)-amino]-biphenyl-4-carbonyl}-amino)-pentanedioic acid in 85.6% yield (251 mg). MS (ESI) m/z 437.

Workup

  1. customThe cooling bath was removed
  2. additionafter the addition
  3. customAfter removing solvent
  4. washthe residue was washed 3 times with EtOAc
  5. customThe solid was then dried under vacuum

Sources & evidence

ORD record
ord-ad1cd2e54f104446aac6e9d5966daf37
Source dataset
uspto-grants-2011_08
Patent number
US07998965B2

Reaction notes

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