Methyl bromoacetate → [tert-Butoxycarbonyl-(3,4-difluorophenyl)-amino]-acetic acid methyl ester

HRID 1267908Notes

Reaction equation

HRID 1267908 reaction equation
[C:1]([O:5][C:6](=[O:16])[NH:7][C:8]1[CH:13]=[CH:12][C:11]([F:14])=[C:10]([F:15])[CH:9]=1)([CH3:4])([CH3:3])[CH3:2].CC(C)([O-])C.[K+].Br[CH2:24][C:25]([O:27][CH3:28])=[O:26]>O1CCCC1>[CH3:28][O:27][C:25](=[O:26])[CH2:24][N:7]([C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:16])[C:8]1[CH:13]=[CH:12][C:11]([F:14])=[C:10]([F:15])[CH:9]=1

Participants

5

Reactant 3

HCID 60984Methyl bromoacetateHCID 2783369Carbamic acid, (3,4-difluorophenyl)-, 1,1-dimethylethyl esterHCID 23665647Potassium tert-butoxide

Product 1

HCID 54030684[tert-Butoxycarbonyl-(3,4-difluorophenyl)-amino]-acetic acid methyl ester

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of (3,4-difluorophenyl)-carbamic acid tert-butyl ester (Tetrahedron, (1992), 48(35), 7373) (15.1 g) in tetrahydrofuran (120 ml) at 0° C. was added potassium tert-butoxide (94 ml of a 1.0 M solution in tetrahydrofuran) dropwise. After stirring for 2 hr methyl bromoacetate (9.1 ml) was added dropwise and ice-bath removed and reaction mixture stirred at room temperature overnight. Reaction mixture concentrated under reduced pressure, diluted with ethyl acetate and washed with water and brine, dried (Na2SO4) and concentrated to leave the sub-title compound as a brown oil (18.0 g).

Workup

  1. additionwas added dropwise
  2. customice-bath removed
  3. customreaction mixture
  4. customReaction mixture
  5. concentrationconcentrated under reduced pressure
  6. additiondiluted with ethyl acetate
  7. washwashed with water and brine
  8. dry with materialdried (Na2SO4)
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-302bd5a608e94b5ca6ff9967c6d1887a
Source dataset
uspto-grants-2003_04
Patent number
US06555541B1

Reaction notes

Loading…