HCID 68157024, compound → HCID 68157973, compound

HRID 242999Notes

Reaction equation

HRID 242999 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:11][CH:10]([NH:12][C:13]2[CH:18]=[C:17]([F:19])[CH:16]=[CH:15][C:14]=2[N+:20]([O-])=O)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>CCOC(C)=O>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH:10]([NH:12][C:13]2[CH:18]=[C:17]([F:19])[CH:16]=[CH:15][C:14]=2[NH2:20])[CH2:11]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

3

Reactant 1

HCID 68157024HCID 68157024, compound

Product 1

HCID 68157973HCID 68157973, compoundYield 100.6%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 3-(5-fluoro-2-nitrophenylamino)azetidine-1-carboxylic acid tert-butyl ester (4.84 g, 15.54 mmol) in EtOAc (100 mL) was degassed with a stream of nitrogen prior to addition of 10% Pd/C (500 mg) and was stirred at RT under a hydrogen atmosphere for 16 h. Additional 10% Pd/C (500 mg) was added and stirring under a hydrogen atmosphere continued for 6 h. The mixture was filtered and the filtrate concentrated in vacuo to afford the title compound as a brown foam (4.4 g, quantitative). LCMS (Method J): RT 2.39 and 2.60 min [M+H]+ 282.1.

Workup

  1. customwas degassed with a stream of nitrogen
  2. additionto addition of 10% Pd/C (500 mg)
  3. additionAdditional 10% Pd/C (500 mg) was added
  4. stirringstirring under a hydrogen atmosphere
  5. waitcontinued for 6 h
  6. filtrationThe mixture was filtered
  7. concentrationthe filtrate concentrated in vacuo

Sources & evidence

ORD record
ord-5c9dce05080b424bb6f2a57174d9f0ff
Source dataset
uspto-grants-2014_02
Patent number
US08653089B2

Reaction notes

Loading…