Trifluoroacetic acid → (9H-Fluoren-9-yl)methyl (4-aminophenyl)carbamate

HRID 2098269Notes

Reaction equation

HRID 2098269 reaction equation
C(O)(C(F)(F)F)=O.C(OC([NH:15][C:16]1[CH:21]=[CH:20][C:19]([NH:22][C:23]([O:25][CH2:26][CH:27]2[C:39]3[CH:38]=[CH:37][CH:36]=[CH:35][C:34]=3[C:33]3[C:28]2=[CH:29][CH:30]=[CH:31][CH:32]=3)=[O:24])=[CH:18][CH:17]=1)=O)(C)(C)C>C(Cl)Cl>[NH2:15][C:16]1[CH:17]=[CH:18][C:19]([NH:22][C:23]([O:25][CH2:26][CH:27]2[C:39]3[CH:38]=[CH:37][CH:36]=[CH:35][C:34]=3[C:33]3[C:28]2=[CH:29][CH:30]=[CH:31][CH:32]=3)=[O:24])=[CH:20][CH:21]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 131730600HCID 131730600, compound

Product 1

HCID 11450338(9H-Fluoren-9-yl)methyl (4-aminophenyl)carbamateYield 99.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

TFA (55.30 mL, 717.76 mmol, 15.0 eq) is added at 0° C. to a stirred solution of (tert-butoxy)-N-{4-[(fluoren-9-ylmethoxy)carbonylamino]phenyl}carboxamide (20.60 g, 47.85 mmol, 1.0 eq) in CH2Cl2 (900 mL). The resulting solution is allowed to warm to room temperature. After stirring overnight at room temperature, the reaction mixture is concentrated to dryness and the residue is triturated in water. Then the mixture is filtered to afford 15.80 g of the expected crude product as a white powder.

Workup

  1. concentrationthe reaction mixture is concentrated to dryness
  2. customthe residue is triturated in water
  3. filtrationThen the mixture is filtered

Sources & evidence

ORD record
ord-68db198bd6bf422aa561091dc14b6ab5
Source dataset
uspto-grants-2013_05
Patent number
US08450477B2

Reaction notes

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