Water → HCID 70071791, compound

HRID 1977579Notes

Reaction equation

HRID 1977579 reaction equation
[CH2:1]([O:3][C:4]([NH:6][CH:7]([C:13]([O:15]C)=[O:14])[CH2:8][CH:9]1[CH2:12][CH2:11][CH2:10]1)=[O:5])[CH3:2].O.[OH-].[Na+]>C1C=CC=CC=1>[CH2:1]([O:3][C:4]([NH:6][C@H:7]([C:13]([OH:15])=[O:14])[CH2:8][CH:9]1[CH2:10][CH2:11][CH2:12]1)=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 21993439HCID 21993439, compound

Product 1

HCID 70071791HCID 70071791, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

10.8 g (47 mmol) of methyl ethoxycarbonyl-3-cyclobutyl-DL-alaninate (synthesised in Step B) is dissolved in 20 ml of benzene in the 250 ml vessel of the titrator. 100 ml of water is added and the pH of the solution is adjusted to 7.5 with 1M NaOH under stirring. 40 mg of enzyme [Subtilisin Carlsberg, Protease, Type VIII (Sigma)] is added, the pH readjusted to 7.5 and kept at this value during titration. The enzymatic hydrolysis is complete in 3 hours. The phases are separated. From the aqueous phase pure ethoxy-carbonyl-3-cyclobutyl-L-alanine can be isolated. The benzene phase is washed with 2×10 ml of 5% NaHCO3 and 2×10 ml of water, dried over anhydrous sodium sulphate and evaporated at a pressure of 2.0-2.5 kPa. The resulting yellowish oil is considered to be pure and used without further treatment in the next step.

Workup

  1. customThe enzymatic hydrolysis
  2. customThe phases are separated

Sources & evidence

ORD record
ord-1fb5224e5dda4cd2a31931869b25203b
Source dataset
uspto-grants-2001_05
Patent number
US06235707B1

Reaction notes

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