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

HRID 333104Notes

Reaction equation

HRID 333104 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-e0cb00e501a947efa5abeaf6a020cfad
Source dataset
uspto-grants-2014_11
Patent number
US08877961B2

Reaction notes

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