Water → HCID 117812702, compound

HRID 591319Notes

Reaction equation

HRID 591319 reaction equation
Cl.[NH2:2][C@@H:3]([CH2:8][CH2:9][CH:10]([CH2:15][C:16]1[CH:21]=[CH:20][C:19]([OH:22])=[CH:18][CH:17]=1)[C:11]([O:13][CH3:14])=[O:12])[C:4]([O:6][CH3:7])=[O:5].[H-].[Na+].Br[CH2:26][F:27].O>CN(C=O)C>[NH2:2][C@@H:3]([CH2:8][CH2:9][CH:10]([CH2:15][C:16]1[CH:17]=[CH:18][C:19]([O:22][CH2:26][F:27])=[CH:20][CH:21]=1)[C:11]([O:13][CH3:14])=[O:12])[C:4]([O:6][CH3:7])=[O:5]

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 61108BromofluoromethaneHCID 131734512HCID 131734512, compound

Product 1

HCID 117812702HCID 117812702, compoundYield 20.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

Dimethyl (2S)-2-amino-5-(4-hydroxybenzyl)hexanedioate hydrochloride (200 mg, 0.54 mmol) were solved in DMF (5 ml) and at 0° C. sodium hydride (34 mg, 1.14 mmol) were added. After 30 min, bromofluoromethane (1.35 mmol) were added and the resulting mixture was stirred at 0° C. for one hour. The mixture was then poured into water and extracted three times with methylene chloride. The organic phase was dried with sodium sulfate and concentrated in vacuo. The residue was purified by silica gel chromatography to yield 37 mg (20.8%) of the product.

Workup

  1. additionwere added
  2. extractionextracted three times with methylene chloride
  3. dry with materialThe organic phase was dried with sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-86e8e02f875c425f9a9429473ed318f0
Source dataset
uspto-grants-2016_01
Patent number
US09238631B2

Reaction notes

Loading…