Lithium Hydroxide → ((2(S)-Benzoylamino-3-methylbutyryl)benzylamino)acetic Acid

HRID 1456648Notes

Reaction equation

HRID 1456648 reaction equation
C([O:3][C:4](=[O:29])[CH2:5][N:6]([C:14](=[O:28])[C@@H:15]([NH:19][C:20](=[O:27])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[CH:16]([CH3:18])[CH3:17])[CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)C.[Li+].[OH-]>CO>[C:20]([NH:19][C@@H:15]([CH:16]([CH3:18])[CH3:17])[C:14]([N:6]([CH2:5][C:4]([OH:29])=[O:3])[CH2:7][C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)=[O:28])(=[O:27])[C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 53936603((2(S)-Benzoylamino-3-methylbutyryl)benzylamino)acetic Acid Ethyl Ester

Product 1

HCID 53859725((2(S)-Benzoylamino-3-methylbutyryl)benzylamino)acetic AcidYield 92.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of compound 703 (3.45 g, 8.8 mmol) in MeOH (9 mL) was added 1N LiOH (9 mL) and the reaction allowed to stir over night. The reaction was concentrated in vacuo and the residue taken up into EtOAc and H2 O. The layers were separated and the aqueous phase was acidified with 1N HCl. The product was extracted with EtOAc (2×). The extracts were combined, washed with brine, dried over MgSO4, filtered and concentrated in vacuo to provide 3.0 g of compound 704. ##STR83##

Workup

  1. concentrationThe reaction was concentrated in vacuo
  2. customThe layers were separated
  3. extractionThe product was extracted with EtOAc (2×)
  4. washwashed with brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-25ec1642ce0b40c78066ac5efb2ee3b8
Source dataset
uspto-grants-1998_12
Patent number
US05843904

Reaction notes

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