Diethyl 2-t-butyloxycarbonylamino-2-(benzyloxycarbonylmethyl)malonate → (R)-1-benzyl hydrogen 3-t-butyloxycarbonylamino-3-ethoxycarbonylsuccinate

HRID 57752Notes

Reaction equation

[C:1]([O:5][C:6]([NH:8][C:9]([CH2:20][C:21]([O:23][CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)=[O:22])([C:15]([O:17]CC)=[O:16])[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:15]([OH:17])=[O:16])[CH2:20][C:21]([O:23][CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)=[O:22])=[O:7])([CH3:3])([CH3:4])[CH3:2]

Participants

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-(benzyloxycarbonylmethyl)malonate (1.0 g) dissolved in acetonitrile (10 mL). The mixture was stirred at 30° C. for 4 hours to produce the title compound. Optical purity measured by HPLC was 78.1% ee. 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

custom1.0 g of pig liver esterase produced by Sigma [PLE (27 kU/g), lyophilized product, product number: E3019]

Sources & evidence

ORD record: ord-97e63dce37f24e41bd0669010e1bb380
Source dataset: uspto-grants-2016_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09434737B2

Reaction notes

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