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

HRID 527385Notes

Reaction equation

HRID 527385 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) was added at 0° C. to a stirred solution of (tert-butoxy)-N-{4-[(fluoren-9-yl-methoxy)carbonylamino]phenyl}carboxamide (20.60 g, 47.85 mmol, 1.0 eq) in CH2Cl2 (900 mL). The resulting solution was allowed to come at room temperature. After stirring overnight at room temperature, the reaction mixture was concentrated to dryness and the residue was triturated in water. Then the mixture was filtered to afford 15.80 g of the expected crude product as a white powder.

Workup

  1. customto come at room temperature
  2. concentrationthe reaction mixture was concentrated to dryness
  3. customthe residue was triturated in water
  4. filtrationThen the mixture was filtered

Sources & evidence

ORD record
ord-99f524d309bc41718bcb41e42f20fd6b
Source dataset
uspto-grants-2016_05
Patent number
US09346799B2

Reaction notes

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