Sodium Hydroxide → HCID 69545630, compound

HRID 1743646Notes

Reaction equation

HRID 1743646 reaction equation
C[O:2][C:3](=[O:23])[C@H:4]([CH2:13][S:14][C:15]1[CH:20]=[CH:19][C:18]([Br:21])=[CH:17][C:16]=1[NH2:22])[NH:5][C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7].[OH-].[Na+]>CC(OC)(C)C>[NH2:22][C:16]1[CH:17]=[C:18]([Br:21])[CH:19]=[CH:20][C:15]=1[S:14][CH2:13][C@@H:4]([NH:5][C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7])[C:3]([OH:23])=[O:2]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 58604709HCID 58604709, compound

Product 1

HCID 69545630HCID 69545630, compound

Reagents, catalysts & solvents 1

HCID 15413tert-Butyl methyl etherSolvent

Procedure

200 mg (0.493 mmol) of N-tert-butoxycarbonyl-3-(4-bromo-2-aminophenylthio)-L-alanine methyl ester (93.8%) was added to a system consisting of 5 ml TBME and 20 ml buffer solution (0.1M sodium chloride; 3 mM sodium phosphate pH 7.0) under vigorous stirring. Enzyme [see following table] was added and the pH maintained at 7.0 under vigorous stirring by the controlled addition (pH-static) of 0.1N sodium hydroxide solution. After termination of the reaction, the reaction mixture was washed twice with 25 ml TBME, acidified to pH 2.5 with 25% HCl and extracted with 3×25 ml ethyl acetate. The combined organic phases were dried over sodium sulfate, the solvent evaporated and the residue dried on a high vacuum.

Workup

  1. additionEnzyme [see following table] was added
  2. temperaturethe pH maintained at 7.0
  3. customAfter termination of the reaction
  4. washthe reaction mixture was washed twice with 25 ml TBME
  5. extractionextracted with 3×25 ml ethyl acetate
  6. dry with materialThe combined organic phases were dried over sodium sulfate
  7. customthe solvent evaporated
  8. customthe residue dried on a high vacuum

Sources & evidence

ORD record
ord-6fcb0c42aac744f1bb0c01a67656ddd1
Source dataset
uspto-grants-2006_03
Patent number
US07011960B2

Reaction notes

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