Hexane → (R)-2-benzyloxycarbonylamino-2-ethoxycarbonylsuccinimide

HRID 1671700Notes

Reaction equation

HRID 1671700 reaction equation
COC(C)(C)C.CCCCCC.[CH2:13]([O:20][C:21]([NH:23][C:24]1([C:31]([O:33][CH2:34][CH3:35])=[O:32])[CH2:29][C:28](=[O:30])[NH:27][C:25]1=[O:26])=[O:22])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>P([O-])([O-])([O-])=O.O1CCCC1>[CH2:13]([O:20][C:21]([NH:23][C@:24]1([C:31]([O:33][CH2:34][CH3:35])=[O:32])[CH2:29][C:28](=[O:30])[NH:27][C:25]1=[O:26])=[O:22])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

6

Reactant 3

HCID 8058HexaneHCID 15413tert-Butyl methyl etherHCID 10267979Ethyl 3-(((benzyloxy)carbonyl)amino)-2,5-dioxopyrrolidine-3-carboxylate

Product 1

HCID 9944916(R)-2-benzyloxycarbonylamino-2-ethoxycarbonylsuccinimideYield 36%

Reagents, catalysts & solvents 2

HCID 1061PhosphateSolventHCID 8028TetrahydrofuranSolvent

Procedure

0.5 g of esterase (PLE (21 kU/g); manufactured by Sigma-Aldrich Corporation, lyophilized powder) were dissolved in 200 mL of 0.07 mol/L phosphate buffer solution of which pH value was adjusted to 6-5 and thereto, a solution in which 10 g of 2-benzyloxycarbonylamino-2-ethoxycarbonyl succinimide were dissolved in 20 g of tetrahydrofuran was added. The resultant mixture was stirred at 30° C. for 48 hours and thereto, 100 mL of t-butyl methyl ether were added. Thereafter, the resultant mixture was filtered with Celite (No. 545) and washed with 50 mL of t-butyl methyl ether. After the filtrate was removed, the organic phase was washed with 100 ml, of water several times and the solvent was distilled off under reduced pressure. Thereafter, the product was recrystallized in ethyl acetate and hexane to thereby obtaining 3.6 g (yield: 36%) of (R)-2-benzyloxycarbonylamino-2-ethoxycarbonyl succinimide having an optical purity of 98.9% e.e. (enantiomeric excess) as a white crystal.

Workup

  1. additionwas added
  2. filtrationThereafter, the resultant mixture was filtered with Celite (No
  3. wash545) and washed with 50 mL of t-butyl methyl ether
  4. customAfter the filtrate was removed
  5. washthe organic phase was washed with 100 ml, of water several times
  6. distillationthe solvent was distilled off under reduced pressure
  7. customThereafter, the product was recrystallized in ethyl acetate

Sources & evidence

ORD record
ord-516b108b73c046fe84a54bc7c07c1183
Source dataset
uspto-grants-2011_08
Patent number
US07994342B2

Reaction notes

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