Ethyl bromoacetate → HCID 54537755, compound

HRID 322526Notes

Reaction equation

HRID 322526 reaction equation
[C:1]([O:5][C:6](=[O:15])[NH:7][C@H:8]1[CH2:12][C@@H:11]([CH3:13])[NH:10][C:9]1=[O:14])([CH3:4])([CH3:3])[CH3:2].C[Si]([N-][Si](C)(C)C)(C)C.[Na+].Br[CH2:27][C:28]([O:30][CH2:31][CH3:32])=[O:29].[NH4+].[Cl-]>C1COCC1>[CH2:31]([O:30][C:28](=[O:29])[CH2:27][N:10]1[C@H:11]([CH3:13])[CH2:12][C@H:8]([NH:7][C:6]([O:5][C:1]([CH3:2])([CH3:4])[CH3:3])=[O:15])[C:9]1=[O:14])[CH3:32]

Participants

6

Reactant 4

HCID 7748Ethyl bromoacetateHCID 25517Ammonium ChlorideHCID 2724254Sodium bis(trimethylsilyl)amideHCID 54130332HCID 54130332, compound

Product 1

HCID 54537755HCID 54537755, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 13-7 (1.83 g, 8.4 mmol) in THF (22 mL) at −78° C. was added sodium bis(trimethylsilyl)amide (9.4 mL, 9.4 mmol; 1M/THF) dropwise. After an additional 20 min, ethyl bromoacetate (1.13 mL, 10.3 mmol) was added dropwise. After an additional 20 minutes, the mixture was allowed to warm to 0° C., and 20 mL sat. aqueous NH4Cl was added. The layers were separated, the aqueous layer washed with EtOAc, and the combined organic extracts were dried over K2CO3. Following evaporative removal of the solvent, the residue was chromatographed (silica gel, 40% ethyl acetate/hexanes) to give 13-8 as a colorless oil.

Workup

  1. waitAfter an additional 20 minutes
  2. customThe layers were separated
  3. washthe aqueous layer washed with EtOAc
  4. dry with materialthe combined organic extracts were dried over K2CO3
  5. customremoval of the solvent
  6. customthe residue was chromatographed (silica gel, 40% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-779a806be33f4024841d916c465fe753
Source dataset
uspto-grants-2001_04
Patent number
US06211184B1

Reaction notes

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