Benzyl Bromide → Boc-Ser-OBzl

HRID 2217143Notes

Reaction equation

HRID 2217143 reaction equation
[C:1]([NH:8][C@H:9]([C:12]([OH:14])=[O:13])[CH2:10][OH:11])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[CH2:15](Br)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C>[CH2:15]([O:13][C:12](=[O:14])[C@H:9]([CH2:10][OH:11])[NH:8][C:1]([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 10796Cesium carbonateHCID 98766N-[tert-butoxycarbonyl]-L-serine

Product 1

HCID 7018792Boc-Ser-OBzl

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In a round-bottomed flask were placed N-BocSerine (20.0 g, 89.605 mmol, 1 eq.), benzyl bromide (10.76 ml, 90.50 mmol, 1.01 eq.) and cesium carbonate (56.64 g, 173.84 mmol, 1.94 eq.) in DMF (180 mL). The suspension was stirred under nitrogen at room temperature for 2 hrs to overnight. The mixture was partitioned between water and ethyl acetate (1:1, 1000 ml) and aqueous layer was re-extracted with ethyl acetate (2×200 mL). The combined organic layers were washed with water (2×500 mL), saturated sodium chloride, and dried over sodium sulfate. The solvents were removed in vacuo and the crude material purified on silica gel to get N-Boc-serine benzyl ester.

Workup

  1. customIn a round-bottomed flask were placed
  2. customThe mixture was partitioned between water and ethyl acetate (1:1, 1000 ml) and aqueous layer
  3. extractionwas re-extracted with ethyl acetate (2×200 mL)
  4. washThe combined organic layers were washed with water (2×500 mL), saturated sodium chloride
  5. dry with materialdried over sodium sulfate
  6. customThe solvents were removed in vacuo
  7. customthe crude material purified on silica gel

Sources & evidence

ORD record
ord-257c1248422141ba8cd742f14136ac78
Source dataset
uspto-grants-2008_08
Patent number
US07407952B2

Reaction notes

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