Hydrochloric Acid → Z-Val-pro-OH

HRID 1471296Notes

Reaction equation

HRID 1471296 reaction equation
C[O:2][C:3](=[O:26])[C@@H:4]1[CH2:8][CH2:7][CH2:6][N:5]1[C:9](=[O:25])[C@H:10]([CH:22]([CH3:24])[CH3:23])[NH:11][C:12]([O:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[O:13].[Li+].[OH-].Cl>C1COCC1>[C:12]([NH:11][C@H:10]([C:9]([N:5]1[CH2:6][CH2:7][CH2:8][C@H:4]1[C:3]([OH:26])=[O:2])=[O:25])[CH:22]([CH3:24])[CH3:23])([O:14][CH2:15][C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1)=[O:13]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 14032133(S)-Methyl 1-((S)-2-(((benzyloxy)carbonyl)amino)-3-methylbutanoyl)pyrrolidine-2-carboxylate

Product 1

HCID 10783923Z-Val-pro-OH

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of N-Cbz-valylproline methyl ester (Cbz-NH-[VP]-CO2CH3) (3.62 g, 10 mmol) in THF (10 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 (20 mL) and ethyl acetate (20 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 (20 mL) and ethyl acetate (20 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-19f4d11647544655a8bde73bcb96ecea
Source dataset
uspto-grants-2015_04
Patent number
US09011918B2

Reaction notes

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