Water → Boc-hyp-obzl

HRID 1662722Notes

Reaction equation

HRID 1662722 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:15][C@H:14]([OH:16])[CH2:13][C@H:9]1[C:10]([OH:12])=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].C([O-])(O)=O.[Na+].[CH2:22](Br)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.O>CN(C=O)C>[OH:16][C@H:14]1[CH2:15][N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:7])[C@H:9]([C:10]([O:12][CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[O:11])[CH2:13]1

Participants

6

Reactant 4

HCID 962WaterHCID 7498Benzyl BromideHCID 88804(2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acidHCID 516892Sodium Bicarbonate

Product 1

HCID 11902907Boc-hyp-obzl

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of (4R)-1-(tert-butoxy carbonyl)-4-hydroxy-L-proline in DMF (80 ml) was added 5.4 g of NaHCO3 and 11.1 g of benzyl bromide and the reaction mixture was stirred at 60° C. for 5 hours. Water was added to the reaction solution and the resulting mixture was extracted with EtOAc. The extract was dried over Na2SO4, then, the drying agent was separated by filtration and the solvent was evaporated under reduced pressure. The obtained residue was purified by column chromatography (silicagel 60; mobile phase: hexane/EtOAc=1/1 to CHCl3/MeOH=8/1; v/v) to obtain 10.0 g of the title compound (colorless oil).

Workup

  1. extractionthe resulting mixture was extracted with EtOAc
  2. dry with materialThe extract was dried over Na2SO4
  3. customthe drying agent was separated by filtration
  4. customthe solvent was evaporated under reduced pressure
  5. customThe obtained residue was purified by column chromatography (silicagel 60; mobile phase: hexane/EtOAc=1/1 to CHCl3/MeOH=8/1; v/v)

Sources & evidence

ORD record
ord-7990622d00754ef7a96bdda2b81406a7
Source dataset
uspto-grants-2011_10
Patent number
US08030499B2

Reaction notes

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