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

HRID 471339
Notes
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Reaction equation

HRID 471339 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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 1

HCID 66725114Diethyl 2-benzyloxycarbonylamino-2-ethoxycarbonylsuccinate

Product 1

HCID 66725113(R)-1-ethyl hydrogen 3-benzyloxycarbonylamino-3-ethoxycarbonylsuccinateYield 84%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 1061PhosphateSolvent

Conditions

Temperature
30 °C

Procedure

4.0 g of pig liver esterase produced by Sigma [PLE (27 kU/g), lyophilized product, product number: E30191 was dissolved in a 0.05 mol/L phosphate buffer adjusted to pH 6.5 (360 mL), and the solution was added with a solution of diethyl 2-benzyloxycarbonylamino-2-ethoxycarbonylsuccinate (4.0 g) dissolved in ethanol (40 mL). The mixture was stirred at 30° C. for 20 hours to obtain (R)-1-ethyl hydrogen 3-benzyloxycarbonylamino-3-ethoxycarbonylsuccinate at a yield of 84% and optical purity of 93.6% ee.

Workup

  1. custom4.0 g of pig liver esterase produced by Sigma [PLE (27 kU/g)

Sources & evidence

ORD record
ord-ef701c50889748888e4b11c1b11af531
Source dataset
uspto-grants-2014_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08633001B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes