Ethyl Acetate → Methyl 2-((3-(4-bromophenyl)-2-((tert-butoxycarbonyl)amino)propoxy)methyl)-benzoate

HRID 1429362Notes

Reaction equation

HRID 1429362 reaction equation
[C:1]([O:5][C:6](=[O:19])[NH:7][CH:8]([CH2:17][OH:18])[CH2:9][C:10]1[CH:15]=[CH:14][C:13]([Br:16])=[CH:12][CH:11]=1)([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].Br[CH2:23][C:24]1[CH:33]=[CH:32][CH:31]=[CH:30][C:25]=1[C:26]([O:28][CH3:29])=[O:27].CC(=O)OCC>C1COCC1>[Br:16][C:13]1[CH:12]=[CH:11][C:10]([CH2:9][CH:8]([NH:7][C:6]([O:5][C:1]([CH3:3])([CH3:2])[CH3:4])=[O:19])[CH2:17][O:18][CH2:23][C:24]2[CH:33]=[CH:32][CH:31]=[CH:30][C:25]=2[C:26]([O:28][CH3:29])=[O:27])=[CH:15][CH:14]=1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 2734813Methyl 2-(bromomethyl)benzoateHCID 57594209tert-Butyl 3-(4-bromophenyl)-1-hydroxypropan-2-ylcarbamate

Product 1

HCID 67382431Methyl 2-((3-(4-bromophenyl)-2-((tert-butoxycarbonyl)amino)propoxy)methyl)-benzoateYield 34%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of compound 3f (6.6 g, 20 mmol) in dry THF (100 mL) was added NaH (60%, 960 mg, 24 mmol) in small portions at 0° C. and stirred for 1 hr. Then compound 3b (5 g, 22 mmol) in THF (50 mL) was added dropwise, and the reaction mixture was allowed to stir at rt overnight. The reaction was quenched with water and extracted with EA (2×100 mL). The combined organic extracts were dried over anhydrous Na2SO4 and concentrated under reduced pressure. The residue was purified by CC eluting with PE:EA=9:1 to give 3g as a white solid (3.2 g, 34% yield).

Workup

  1. stirringto stir at rt overnight
  2. customThe reaction was quenched with water
  3. extractionextracted with EA (2×100 mL)
  4. dry with materialThe combined organic extracts were dried over anhydrous Na2SO4
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by CC
  7. washeluting with PE

Sources & evidence

ORD record
ord-1a31c6c7eb334efba815538644671012
Source dataset
uspto-grants-2015_01
Patent number
US08940722B2

Reaction notes

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