Water → HCID 68869657, compound

HRID 2111968Notes

Reaction equation

HRID 2111968 reaction equation
[C:1]1([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH:6]=[CH:5][C:4]([C:7]([NH:9][CH2:10][C:11]2[CH:12]=[C:13]([NH:17]C(=O)OC(C)(C)C)[CH:14]=[CH:15][CH:16]=2)=[O:8])=[CH:3][CH:2]=1.FC(F)(F)C(O)=O.O>C(Cl)Cl>[NH2:17][C:13]1[CH:12]=[C:11]([CH:16]=[CH:15][CH:14]=1)[CH2:10][NH:9][C:7]([C:4]1[CH:5]=[CH:6][C:1]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[CH:2][CH:3]=1)=[O:8]

Participants

5

Reactant 3

HCID 962WaterHCID 6422Trifluoroacetic acid2×HCID 86601922HCID 86601922, compound

Product 1

HCID 68869657HCID 68869657, compoundYield 102%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

tert-Butyl 3-{[(1,1′-biphenyl-4-ylcarbonyl)amino]methyl}phenylcarbamate (250 mg, 0.6 mmol) was dissolved in DCM (10 ml). Trifluoroacetic acid (0.2 ml) was added. The mixture was stirred overnight. HPLC showed that more than 50% of the starting material was not reacted. More trifluoroacetic acid (0.3 ml) was added. The mixture was stirred overnight again. Water was added into the mixture. The phases were not clear. DCM was evaporated in vacuum Ethyl acetate was added to the residue. The obtained organic phase was washed with water (×3) and dried with magnesium sulphate. The solvent was then evaporated. Solid product (185 mg) was obtained, yield 99%.

Workup

  1. customwas not reacted
  2. stirringThe mixture was stirred overnight again
  3. customDCM was evaporated in vacuum Ethyl acetate
  4. additionwas added to the residue
  5. washThe obtained organic phase was washed with water (×3)
  6. dry with materialdried with magnesium sulphate
  7. customThe solvent was then evaporated

Sources & evidence

ORD record
ord-20318f0ee89d41169e59d27363c6a2c1
Source dataset
uspto-grants-2009_04
Patent number
US07521461B2

Reaction notes

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