Sodium Hydroxide → HCID 86708467, compound

HRID 921618Notes

Reaction equation

HRID 921618 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([NH:13][C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[C:11]=1[Cl:12])[C:5](OC)=[O:6].[H-].[Al+3].[Li+].[H-].[H-].[H-].[OH-].[Na+].[O-]S([O-])(=O)=O.[Mg+2]>C1COCC1.CCOCC.O>[Br:1][C:2]1[C:11]([Cl:12])=[C:10]([NH:13][C:14](=[O:15])[O:16][C:17]([CH3:18])([CH3:19])[CH3:20])[CH:9]=[C:4]([CH2:5][OH:6])[CH:3]=1

Participants

8

Reactant 4

HCID 14798Sodium HydroxideHCID 24083Sulfuric acid magnesium salt (1:1)HCID 21226445Aluminium lithium hydrideHCID 86708461HCID 86708461, compound2×

Product 1

HCID 86708467HCID 86708467, compoundYield 88.4%

Reagents, catalysts & solvents 3

HCID 962WaterSolvent2×HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

(I8A): Methyl 3-bromo-5-((tert-butoxycarbonyl)amino)-4-chlorobenzoate (5 g, 13.71 mmol, Intermediate 4) was dissolved in THF (91 mL) at 0° C. under N2. Lithium aluminum hydride solution (10 ml, 10.00 mmol, 1 M in THF) was added dropwise. The reaction mixture was stirred for 2 hours at which point reaction appeared complete by LC/MS. Water (1.4 mL) was added slowly and resulted in a vigorous quench. 1 M aq. NaOH soln (1.4 mL) was added dropwise, followed by a final addition of H2O (4.2 mL). The mixture was stirred vigorously for 15 minutes and then several scoops of MgSO4 were added. The reaction was diluted with Et2O, stirred for 1 hour and then filtered through celite. Concentrated afforded tert-butyl (3-bromo-2-chloro-5-(hydroxymethyl)phenyl)carbamate (4.08 g).

Workup

  1. customresulted in a vigorous quench
  2. stirringThe mixture was stirred vigorously for 15 minutes
  3. stirringstirred for 1 hour
  4. filtrationfiltered through celite
  5. concentrationConcentrated

Sources & evidence

ORD record
ord-ae6b7305053f4229b251a5e81ce182ec
Source dataset
uspto-grants-2016_03
Patent number
US09273057B2

Reaction notes

Loading…