Ethyl bromoacetate → HCID 14975959, compound

HRID 1736683Notes

Reaction equation

HRID 1736683 reaction equation
CC(C)([O-])C.[K+].[C:7]([O:11][C:12]([NH:14][C:15]1[C:20]([N+:21]([O-:23])=[O:22])=[CH:19][CH:18]=[CH:17][C:16]=1[F:24])=[O:13])([CH3:10])([CH3:9])[CH3:8].Br[CH2:26][C:27]([O:29][CH2:30][CH3:31])=[O:28]>C1COCC1>[CH2:30]([O:29][C:27](=[O:28])[CH2:26][N:14]([C:12]([O:11][C:7]([CH3:10])([CH3:8])[CH3:9])=[O:13])[C:15]1[C:20]([N+:21]([O-:23])=[O:22])=[CH:19][CH:18]=[CH:17][C:16]=1[F:24])[CH3:31]

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 10377686HCID 10377686, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 14975959HCID 14975959, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Potassium tert-butoxide (1 M in THF, 8,67 ml) is added (dropwise over 5 min) to a solution of N-(tert-butyloxycarbonyl)-2-fluoro-6-nitroaniline (XIX, EXAMPLE 21, 1.85 g) in THF (15 ml) cooled at 0°. After 20 min, ethyl bromoacetate (0.96 ml) is added dropwise over several minutes. The ice bath is removed and the reaction is stirred for 2 h, after which it is partitioned between ethyl acetate, aqueous sodium bicarbonate and saline. The phases are separated, the organic phase is dried over magnesium sulfate and concentrated to give the title compound, NMR (CDCl3) 1.26, 1.35, 1.50, 3.98, 4.10, 4.20, 4.42, 4.45, 7.42 and 7.39 δ.

Workup

  1. temperaturecooled at 0°
  2. customThe ice bath is removed
  3. customafter which it is partitioned between ethyl acetate, aqueous sodium bicarbonate and saline
  4. customThe phases are separated
  5. dry with materialthe organic phase is dried over magnesium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-b3fbb7edcc6346d29355977ef66272fa
Source dataset
uspto-grants-1996_07
Patent number
US05541324

Reaction notes

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