Sodium Hydroxide → HCID 86644628, compound

HRID 1662061Notes

Reaction equation

HRID 1662061 reaction equation
[OH:1][C@H:2]1[CH2:6][CH2:5][CH2:4][C@@H:3]1[NH:7][C:8](=[O:17])[O:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.Br[CH2:19][C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21].[OH-].[Na+]>C1C=CC=CC=1>[CH2:10]([O:9][C:8]([NH:7][C@H:3]1[CH2:4][CH2:5][CH2:6][C@@H:2]1[O:1][CH2:19][C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])=[O:17])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 79177tert-Butyl bromoacetateHCID 11075389HCID 11075389, compound

Product 1

HCID 86644628HCID 86644628, compoundYield 67.3%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

To a mixture of benzyl [(1S,2S)-2-hydroxycyclopentyl]carbamate (1.3 g) and benzene (13 ml) were added, tert-butyl bromoacetate (3.2 g), hydrogen tetrabutyl ammonium sulfate (0.46 g), and a 50% aqueous NaOH solution (13 ml) under ice-cooling, followed by stirring under ice-cooling for 1 hour and further at room temperature for 2 hours. The reaction mixture was poured into ice-water, extracted with ethyl acetate, then washed with water and saturated brine in this order, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=10:1→7:1→5:1) to obtain tert-butyl {[(1S,2S)-2-{[(benzyloxy)carbonyl]amino}cyclopentyl]oxy}acetate (1.3 g).

Workup

  1. additionwere added
  2. extractionextracted with ethyl acetate
  3. washwashed with water and saturated brine in this order
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=10:1→7:1→5:1)

Sources & evidence

ORD record
ord-bad093105283488095edfd2069b2b2b4
Source dataset
uspto-grants-2011_10
Patent number
US08030489B2

Reaction notes

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