Phenacyl bromide → HCID 118260105, compound

HRID 1779164Notes

Reaction equation

HRID 1779164 reaction equation
[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:13][C:14]1[CH:19]=[CH:18][C:17]([O:20][CH2:21][C:22]#[C:23][CH3:24])=[CH:16][CH:15]=1)[C:10]([OH:12])=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].Br[CH2:26][C:27]([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)=[O:28].CCN(CC)CC>C(OCC)(=O)C>[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:13][C:14]1[CH:19]=[CH:18][C:17]([O:20][CH2:21][C:22]#[C:23][CH3:24])=[CH:16][CH:15]=1)[C:10]([O:12][CH2:26][C:27](=[O:28])[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)=[O:11])=[O:7])([CH3:3])([CH3:2])[CH3:4]

Participants

5

Reactant 3

HCID 6259Phenacyl bromideHCID 8471TriethylamineHCID 90060209HCID 90060209, compound

Product 1

HCID 118260105HCID 118260105, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

(S)-2-tert-Butoxycarbonylamino-3-(4-but-2-ynyloxy-phenyl)-propionic acid (380 mg) was dissolved in ethyl acetate (5.0 mL). A commercially available reagent of 2-bromoacetophenone (164 mg) and Et3N (115.7 μL) were added and the mixture was stirred at room temperature for 2 days. To the reaction solution was added ethyl acetate and the mixture was washed with water and a saturated brine in this order. The organic layer was dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure. The product was purified by recrystallization in 15% ethyl acetate/n-hexane to obtain 2-oxo-2-phenyl-ethyl (S)-2-tert-butoxycarbonylamino-3-(4-but-2-ynyloxy-phenyl)-propionate (277 mg, yield 89% over 2 steps) as colorless crystal (LCMS m/z 452 (M+1) Rt 232 min.).

Workup

  1. washthe mixture was washed with water
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. distillationThe solvent was distilled off under reduced pressure
  4. customThe product was purified by recrystallization in 15% ethyl acetate/n-hexane

Sources & evidence

ORD record
ord-83ebd294e62045258463911101f16c93
Source dataset
uspto-grants-2016_02
Patent number
US09266853B2

Reaction notes

Loading…