Ethyl bromoacetate → HCID 53687702, compound

HRID 322516Notes

Reaction equation

HRID 322516 reaction equation
[CH3:1][C@H:2]1[NH:6][C:5](=[O:7])[C@@H:4]([CH2:8][CH2:9][C:10]2([CH3:15])[O:14][CH2:13][CH2:12][O:11]2)[CH2:3]1.C1COCC1.C[Si]([N-][Si](C)(C)C)(C)C.[Na+].Br[CH2:32][C:33]([O:35][CH2:36][CH3:37])=[O:34]>CCOC(C)=O>[CH2:36]([O:35][C:33](=[O:34])[CH2:32][N:6]1[C@H:2]([CH3:1])[CH2:3][C@H:4]([CH2:8][CH2:9][C:10]2([CH3:15])[O:14][CH2:13][CH2:12][O:11]2)[C:5]1=[O:7])[CH3:37]

Participants

6

Reactant 4

HCID 7748Ethyl bromoacetateHCID 8028TetrahydrofuranHCID 2724254Sodium bis(trimethylsilyl)amideHCID 18394796HCID 18394796, compound

Product 1

HCID 53687702HCID 53687702, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

To a stirred solution of 11-7 (355 mg, 1.67 mmol) and THF (10 mL) at −78° C. was added NaN(TMS)2 (1.83 mL, 1.83 mmol, 1.0 M in THF). After 20 min, ethyl bromoacetate (0.203 mL, 1.84 mmol) was added and the reaction was warmed to 0° C. After 30 minutes, the reaction mixture was diluted with EtOAc and then washed with H2O, brine, dried (MgSO4), and concentrated to give 11-8 as a yellow oil.

Workup

  1. waitAfter 30 minutes
  2. washwashed with H2O, brine
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-db0a13e459374ceebb34b7fcd17c6e04
Source dataset
uspto-grants-2001_04
Patent number
US06211184B1

Reaction notes

Loading…