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

HRID 471340Notes

Reaction equation

[CH2:1]([O:8][C:9]([NH:11][C:12]([C:24]([O:26]CC)=[O:25])([CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20])[C:13]([O:15][CH2:16][CH3:17])=[O:14])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>P([O-])([O-])([O-])=O.C(O)C>[CH2:1]([O:8][C:9]([NH:11][C@@:12]([C:13]([O:15][CH2:16][CH3:17])=[O:14])([C:24]([OH:26])=[O:25])[CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 30 °C

Procedure

5 mg of rabbit liver esterase produced by Sigma (80 kU/g, lyophilized product, product number: E0887) was dissolved in a 0.05 mol/L phosphate buffer adjusted to pH 6.5 (0.4 mL), and the solution was added with a solution of diethyl 2-benzyloxycarbonylamino-2-ethoxycarbonylsuccinate (5 mg) dissolved in ethanol (0.05 mL). The mixture was stirred at 30° C. for 16 hours to obtain (R)-1-ethyl hydrogen 3-benzyloxycarbonylamino-3-ethoxycarbonylsuccinate at a yield of 52% and optical purity of 94.6% ee.

Workup

custom5 mg of rabbit liver esterase produced by Sigma (80 kU/g, lyophilized product, product number: E0887)

Sources & evidence

ORD record: ord-39bfa069302c4851a2a7da84724ff8f0
Source dataset: uspto-grants-2014_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08633001B2

Reaction notes

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