Water → HCID 10719654, compound

HRID 1844496Notes

Reaction equation

HRID 1844496 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([NH2:8])[CH:5]=[CH:4][C:3]=1[NH:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.[C:17]([O-:20])([O-:19])=O.[K+].[K+].[CH:23]1[CH:28]=[CH:27][C:26]([CH2:29][O:30][C:31](Cl)=[O:32])=[CH:25][CH:24]=1.O>ClCCl>[CH2:10]([N:9]([C:3]1[CH:4]=[CH:5][C:6]([NH:8][C:31]([O:30][CH2:29][C:26]2[CH:27]=[CH:28][CH:23]=[CH:24][CH:25]=2)=[O:32])=[CH:7][C:2]=1[F:1])[C:17](=[O:20])[O:19][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1

Participants

6

Reactant 4

HCID 962WaterHCID 10387Benzyl chloroformateHCID 11430Potassium CarbonateHCID 10846382HCID 10846382, compound

Product 1

HCID 10719654HCID 10719654, compoundYield 152%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

7 g (217.3 mmol) of N-(2-fluoro-4-aminophenyl)-N-benzyl amine (4) obtained from the aforesaid process was dissolved in 500 mL dichloromethane, then 60 g (434.6 mmol) of K2CO3 was added thereto, with stirring in an ice bath for 10 minutes. 92 mL (652 mmol) Cbz-Cl was dropped slowly to the mixture over 1 hour and then the mixture was warmed to room temperature. After completion of the reaction, 200 mL water was added to the reaction solution under stirring for 1 hour. The resultant mixture was allowed to stand for separation, and the dichloromethane layer was washed in sequence with 10% diluted hydrochloric acid and NaHCO3 solution. The obtained dichloromethane layer was rotary evaporated to afford a light yellow oil, which was purified with column chromatography to obtain 80 g of a white solid, with a yield of 76.2%.

Workup

  1. additionwas added to the reaction solution
  2. stirringunder stirring for 1 hour
  3. customto stand for separation
  4. washthe dichloromethane layer was washed in sequence with 10% diluted hydrochloric acid and NaHCO3 solution
  5. customThe obtained dichloromethane layer was rotary evaporated
  6. customto afford a light yellow oil, which
  7. customwas purified with column chromatography

Sources & evidence

ORD record
ord-6ce10023f900484aa1c67934c1eab8f5
Source dataset
uspto-grants-2015_02
Patent number
US08946436B2

Reaction notes

Loading…