Benzyl Bromide → HCID 86588486, compound

HRID 1862527Notes

Reaction equation

HRID 1862527 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][C@H:10]([NH:14][C:15](=[O:17])[CH3:16])[C:11]([OH:13])=[O:12])=[O:7])([CH3:4])([CH3:3])[CH3:2].C([O-])(O)=O.[Na+].[CH2:23](Br)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.CCCCCC.C(OCC)(=O)C>CN(C)C=O>[CH2:23]([O:12][C:11](=[O:13])[C@@H:10]([NH:14][C:15](=[O:17])[CH3:16])[CH2:9][NH:8][C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:7])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

6

Reactant 4

HCID 7498Benzyl BromideHCID 516892Sodium BicarbonateHCID 21226206Ethyl acetate hexaneHCID 86588485HCID 86588485, compound

Product 1

HCID 86588486HCID 86588486, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a mixture of N-(t-butoxycarbonyl)-2(S)-acetylamino-β-alanine (3.0 g) in dimethylformamide (60 ml) was added NaHCO3 (2.05 g) at −2° C., and a solution of benzyl bromide in dimethylformamide (60 ml) was added by using a dropping funnel under stirring. The mixture was stirred overnight around 26° C., then poured into a mixture of ice-water (300 ml) and hexane-ethyl acetate (8:2, 500 ml). After the organic layer was separated, the aqueous layer was extracted again with hexane-ethyl acetate (8:2, 300 ml). The combined organic layer was washed with water (300 ml×2), brine (300 ml) and dried over Na2SO4, and evaporated in vacuo. The residue was purified by silica gel chromatography eluting with hexane-ethyl acetate (8:2) to give N-(t-butoxycarbonyl)-2(S)-acetylamino-β-alanine benzyl ester (3.68 g).

Workup

  1. stirringThe mixture was stirred overnight around 26° C.
  2. customAfter the organic layer was separated
  3. extractionthe aqueous layer was extracted again with hexane-ethyl acetate (8:2, 300 ml)
  4. washThe combined organic layer was washed with water (300 ml×2), brine (300 ml)
  5. dry with materialdried over Na2SO4
  6. customevaporated in vacuo
  7. customThe residue was purified by silica gel chromatography
  8. washeluting with hexane-ethyl acetate (8:2)

Sources & evidence

ORD record
ord-66fd100aca7140a7a31ddf56bd3d37f3
Source dataset
uspto-grants-2003_03
Patent number
US06538007B1

Reaction notes

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