Diethyl 2-t-butyloxycarbonylamino-2-ethoxycarbonylsuccinate → (R)-1-ethyl hydrogen 3-t-butyloxycarbonylamino-3-ethoxycarbonylsuccinate

HRID 57747Notes

Reaction equation

HRID 57747 reaction equation
[C:1]([O:5][C:6]([NH:8][C:9]([C:21]([O:23]CC)=[O:22])([CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])[C:10]([O:12][CH2:13][CH3:14])=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2]>P([O-])([O-])([O-])=O.C(#N)C>[C:1]([O:5][C:6]([NH:8][C@@:9]([C:10]([O:12][CH2:13][CH3:14])=[O:11])([C:21]([OH:23])=[O:22])[CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 1

HCID 86661708Diethyl 2-t-butyloxycarbonylamino-2-ethoxycarbonylsuccinate

Product 1

HCID 86661709(R)-1-ethyl hydrogen 3-t-butyloxycarbonylamino-3-ethoxycarbonylsuccinateYield 108.4%

Reagents, catalysts & solvents 2

HCID 1061PhosphateSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
30 °C

Procedure

1.0 g of pig liver esterase produced by Sigma [PLE (27 kU/g), lyophilized product, product number: E3019] was dissolved in a 0.1 mol/L phosphate buffer adjusted to pH 7.5 (90 mL), and the solution was added with a solution of diethyl 2-t-butyloxycarbonylamino-2-ethoxycarbonylsuccinate (1.0 g) dissolved in acetonitrile (10 mL). The mixture was stirred at 30° C. for 4 hours to allow the reaction. After completion of the reaction, the reaction mixture was filtered by using a filtration aid (KC Floc 100) to remove the insoluble matter. The filtrate was cooled, and adjusted to pH 2 by adding 6 mol/L hydrochloric acid, then the objective substance was extracted with ethyl acetate, and the extract was washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure to obtain the title compound (1.0 g).

Workup

  1. custom1.0 g of pig liver esterase produced by Sigma [PLE (27 kU/g), lyophilized product, product number: E3019]
  2. customthe reaction
  3. customAfter completion of the reaction
  4. filtrationthe reaction mixture was filtered
  5. customto remove the insoluble matter
  6. temperatureThe filtrate was cooled
  7. additionby adding 6 mol/L hydrochloric acid
  8. extractionthe objective substance was extracted with ethyl acetate
  9. washthe extract was washed with saturated brine
  10. dry with materialdried over anhydrous magnesium sulfate
  11. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-6c4b611ab3134bb5befd7f925478fec3
Source dataset
uspto-grants-2016_09
Patent number
US09434737B2

Reaction notes

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