Hydrochloric Acid → N-Cbz-valylprolylglycine

HRID 886661Notes

Reaction equation

HRID 886661 reaction equation
C[O:2][C:3](=[O:30])[CH2:4][NH:5][C:6](=[O:29])[C@@H:7]1[CH2:11][CH2:10][CH2:9][N:8]1[C:12](=[O:28])[C@H:13]([CH:25]([CH3:27])[CH3:26])[NH:14][C:15]([O:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=[O:16].[Li+].[OH-].Cl>C1COCC1>[C:15]([NH:14][C@H:13]([C:12]([N:8]1[CH2:9][CH2:10][CH2:11][C@H:7]1[C:6]([NH:5][CH2:4][C:3]([OH:30])=[O:2])=[O:29])=[O:28])[CH:25]([CH3:27])[CH3:26])([O:17][CH2:18][C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1)=[O:16]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 67057640N-Cbz-valylprolylglycine methyl ester

Product 1

HCID 67057723N-Cbz-valylprolylglycine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of N-Cbz-valylprolylglycine methyl ester (Cbz-NH-[VPG]-CO2CH3) (4.2 g, 10 mmol) in THF (20 mL) is added a 1M aqueous solution of LiOH (11 mL, 11 mmol) and the solution is stirred overnight. The resulting solution is acidified to pH about 7 with 1M HCl and the contents of the flask partitioned between water (30 mL) and ethyl acetate (30 mL). The organic phase is extracted with brine, dried over Na2SO4 then concentrated in vacuo to afford the desired compound.

Workup

  1. customthe contents of the flask partitioned between water (30 mL) and ethyl acetate (30 mL)
  2. extractionThe organic phase is extracted with brine
  3. dry with materialdried over Na2SO4
  4. concentrationthen concentrated in vacuo

Sources & evidence

ORD record
ord-60cc155b75f04da7a397973068d24126
Source dataset
uspto-grants-2012_08
Patent number
US08246991B2

Reaction notes

Loading…