Formic Acid → HCID 86646074, compound

HRID 1800693Notes

Reaction equation

HRID 1800693 reaction equation
[C:1]([O:5][C:6](=[O:16])[NH:7][C:8]1[CH:13]=[C:12]([NH2:14])[CH:11]=[CH:10][C:9]=1[F:15])([CH3:4])([CH3:3])[CH3:2].[CH:17](O)=[O:18].C(OC(=O)C)(=O)C.C(=O)([O-])O.[Na+]>O1CCCC1>[F:15][C:9]1[CH:10]=[CH:11][C:12]([NH:14][CH:17]=[O:18])=[CH:13][C:8]=1[NH:7][C:6](=[O:16])[O:5][C:1]([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 284Formic AcidHCID 7918Acetic AnhydrideHCID 516892Sodium BicarbonateHCID 10933172tert-Butyl (5-amino-2-fluorophenyl)carbamate

Product 1

HCID 86646074HCID 86646074, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of tert-butyl(5-amino-2-fluorophenyl)carbamate (10.0 g, 44.2 mmol) in tetrahydrofuran (60 mL) was added a mixture of formic acid (8.34 mL, 221 mmol) and acetic anhydride (5.01 mL, 53.0 mmol), and the mixture was stirred at room temperature for 16 hr. To the reaction mixture was added saturated aqueous sodium hydrogen carbonate solution (100 mL), and the mixture was extracted with ethyl acetate (100 mL, 30 mL). The combined organic layer was washed with saturated brine (10 mL), filtered through a silica gel pad, and the filtrate was concentrated under reduced pressure to give tert-butyl [2-fluoro-5-(formylamino)phenyl]carbamate as a brown oil. The obtained compound was used for the next reaction without further purification.

Workup

  1. extractionthe mixture was extracted with ethyl acetate (100 mL, 30 mL)
  2. washThe combined organic layer was washed with saturated brine (10 mL)
  3. filtrationfiltered through a silica gel pad
  4. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-94c4bd0d8c764cecbd43d362dca44685
Source dataset
uspto-grants-2013_01
Patent number
US08344135B2

Reaction notes

Loading…