Hydrochloric Acid → L-valine p-nitrobenzyl ester hydrochloride

HRID 891699Notes

Reaction equation

HRID 891699 reaction equation
[N+:1]([C:4]1[CH:25]=[CH:24][C:7]([CH2:8][O:9][C:10](=[O:23])[C@H:11]([CH:20]([CH3:22])[CH3:21])[NH:12]C(OC(C)(C)C)=O)=[CH:6][CH:5]=1)([O-:3])=[O:2].[ClH:26]>O1CCOCC1>[ClH:26].[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([CH2:8][O:9][C:10](=[O:23])[C@H:11]([CH:20]([CH3:21])[CH3:22])[NH2:12])=[CH:24][CH:25]=1)([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 13992531N-(t-butoxycarbonyl)-L-valine p-nitrobenzyl ester

Product 1

HCID 69544143L-valine p-nitrobenzyl ester hydrochlorideYield 88%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

To a solution of N-(t-butoxycarbonyl)-L-valine p-nitrobenzyl ester (3.07 g, 8.71 mmol) (obtained as described in Reference Example 46(1)) in 1,4-dioxane (31 ml) was added a solution of 4N hydrogen chloride in 1,4-dioxane (31 ml) in an ice bath, and the mixture was stirred at room temperature overnight. After checking the completion of the reaction, the reaction mixture was concentrated under reduced pressure, to the obtained residue was added ethyl acetate, and the mixture was filtered. The resulting residue was washed with ethyl acetate and dried to give L-valine p-nitrobenzyl ester hydrochloride (2.21 g, yield 88%).

Workup

  1. customthe completion of the reaction
  2. concentrationthe reaction mixture was concentrated under reduced pressure, to the obtained residue
  3. additionwas added ethyl acetate
  4. filtrationthe mixture was filtered
  5. washThe resulting residue was washed with ethyl acetate
  6. customdried

Sources & evidence

ORD record
ord-0dba5b0e768d4b0a8f165c0bd0d6dd66
Source dataset
uspto-grants-2006_02
Patent number
US07001897B2

Reaction notes

Loading…