Lithium diisopropylamide → HCID 68534124, compound

HRID 2096129Notes

Reaction equation

HRID 2096129 reaction equation
C([N-]C(C)C)(C)C.[Li+].[CH2:9]([O:11][C:12](=[O:23])[CH2:13][NH:14][CH2:15][C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH3:10].Br[CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=1[I:32]>O1CCCC1>[C:19]([O:18][C:16]([CH2:15][NH:14][CH:13]([CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=1[I:32])[C:12]([O:11][CH2:9][CH3:10])=[O:23])=[O:17])([CH3:22])([CH3:21])[CH3:20]

Participants

5

Reactant 3

HCID 2724682Lithium diisopropylamideHCID 10921941HCID 10921941, compoundHCID 114264722-Iodobenzyl Bromide

Product 1

HCID 68534124HCID 68534124, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

At −78° C., lithium diisopropylamide solution (2 M in THF/n-heptane, 17 ml, 34 mmol) was slowly added dropwise to ethyl(tert-butoxycarbonylmethylamino)acetate (7.4 g, 34 mmol) in tetrahydrofuran (abs., 50 ml). The mixture was stirred at this temperature for 2 h. 1-Bromomethyl-2-iodobenzene (10.0 g, 46 mmol) was then slowly added dropwise, and the mixture was stirred at −78° C. for 1 h. The reaction solution was slowly (12 h) warmed to room temperature and then concentrated on a rotary evaporator. The residue was taken up in ethyl acetate, washed, dried and concentrated. The residue obtained in this manner was then purified by column chromatography (SiO2, hexane/ethyl acetate). This gave 6.4 g (43%) of the target compound.

Workup

  1. stirringthe mixture was stirred at −78° C. for 1 h
  2. custom(12 h)
  3. concentrationconcentrated on a rotary evaporator
  4. washwashed
  5. customdried
  6. concentrationconcentrated
  7. customThe residue obtained in this manner
  8. customwas then purified by column chromatography (SiO2, hexane/ethyl acetate)

Sources & evidence

ORD record
ord-07ec0adea2f046268bac032586af9dd5
Source dataset
uspto-grants-2013_05
Patent number
US08450301B2

Reaction notes

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