Sodium Hydroxide → HCID 69545603, compound

HRID 1743651Notes

Reaction equation

HRID 1743651 reaction equation
C[O:2][C:3](=[O:28])[C@H:4]([CH2:13][S:14][C:15]1[CH:20]=[CH:19][C:18]([C:21]([O:23][CH2:24][CH:25]=[CH2:26])=[O:22])=[CH:17][C:16]=1[NH2:27])[NH:5][C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7].[OH-].[Na+]>CC(OC)(C)C>[CH2:24]([O:23][C:21](=[O:22])[C:18]1[CH:19]=[CH:20][C:15]([S:14][CH2:13][C@@H:4]([NH:5][C:6]([O:8][C:9]([CH3:11])([CH3:10])[CH3:12])=[O:7])[C:3]([OH:28])=[O:2])=[C:16]([NH2:27])[CH:17]=1)[CH:25]=[CH2:26]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 58604712HCID 58604712, compound

Product 1

HCID 69545603HCID 69545603, compound

Reagents, catalysts & solvents 1

HCID 15413tert-Butyl methyl etherSolvent

Conditions

Temperature
40 °C

Procedure

200 mg (0.487 mmol) of N-tert-butoxycarbonyl-3-(4-alloxycarbonyl-2-aminophenylthio)-L-alanine methyl ester (96.7%) 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 at 40° C. 100 μl of Alcalase 2.4 L [a subtilisin Carlsberg from Novo Nordisk] was added and the pH maintained at 7.0 under vigorous stirring at 40° C. by the controlled addition (pH-static) of 0.1N sodium hydroxide solution. After a consumption 5.44 ml of titrating agent (112% of theory; after 17.4 h), the reaction mixture was washed with 25 ml TBME, acidified to pH 2.5 with IN 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 to give 190 mg (0.479 mmol; 98%) of the product acid in 94.5% HPLC-purity (area-%).

Workup

  1. addition100 μl of Alcalase 2.4 L [a subtilisin Carlsberg from Novo Nordisk] was added
  2. temperaturethe pH maintained at 7.0
  3. customAfter a consumption 5.44 ml of titrating agent (112% of theory; after 17.4 h)
  4. washthe reaction mixture was washed 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
  9. customto give 190 mg (0.479 mmol; 98%) of the product acid in 94.5% HPLC-purity (area-%)

Sources & evidence

ORD record
ord-84548727d2284cfca1b88d286cb55c73
Source dataset
uspto-grants-2006_03
Patent number
US07011960B2

Reaction notes

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