Benzyl chloroformate → HCID 10088792, compound

HRID 1424311Notes

Reaction equation

HRID 1424311 reaction equation
[NH2:1][CH:2]([CH2:6][C:7]1[CH:12]=[CH:11][C:10]([B:13]([OH:15])[OH:14])=[CH:9][CH:8]=1)[C:3]([OH:5])=[O:4].Cl[C:17]([O:19][CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[O:18]>[OH-].[Na+].O1CCOCC1>[CH2:20]([O:19][C:17]([NH:1][CH:2]([CH2:6][C:7]1[CH:12]=[CH:11][C:10]([B:13]([OH:15])[OH:14])=[CH:9][CH:8]=1)[C:3]([OH:5])=[O:4])=[O:18])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

5

Reactant 2

HCID 10387Benzyl chloroformateHCID 53503p-Boronophenylalanine

Product 1

HCID 10088792HCID 10088792, compound

Reagents, catalysts & solvents 2

HCID 14798Sodium HydroxideSolventHCID 312751,4-DioxaneSolvent2×

Procedure

3.0 g (14.4 mmol) of 2-amino-3-(4-boronophenyl)propionic acid were dissolved in 120 ml 0.4 N NaOH solution and diluted with 120 ml 1,4-dioxane. 2.05 ml benzyl chloroformate (14.4 mmol) in 15 ml 1,4-dioxane were added slowly at −15° C. The reaction mixture was allowed to come to room temperature over night and the organic solvent was removed under reduced pressure. After extracting the acidified remaining aqueous phase with ethyl acetate and drying this organic phase over Na2SO4 the solvent was removed under reduced pressure. The crude product was recrystallized from acetonitrile.

Workup

  1. waitto come to room temperature over night
  2. customthe organic solvent was removed under reduced pressure
  3. extractionAfter extracting the
  4. dry with materialdrying this organic phase over Na2SO4 the solvent
  5. customwas removed under reduced pressure
  6. customThe crude product was recrystallized from acetonitrile

Sources & evidence

ORD record
ord-99849043dbc74aeaaa33d455b3aa4d2b
Source dataset
uspto-grants-2015_01
Patent number
US08927534B2

Reaction notes

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