Diethyl Ether → Benzyl (2s)-2-[(4-cyanophenoxy)methyl]-1-aziridinecarboxylate

HRID 411543Notes

Reaction equation

HRID 411543 reaction equation
[OH-].[Na+].CS(O[C@@H:8]([CH2:21][O:22][C:23]1[CH:28]=[CH:27][C:26]([C:29]#[N:30])=[CH:25][CH:24]=1)[CH2:9][NH:10][C:11]([O:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:12])(=O)=O.CCOCC>O.S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.C(Cl)Cl>[C:29]([C:26]1[CH:27]=[CH:28][C:23]([O:22][CH2:21][C@@H:8]2[CH2:9][N:10]2[C:11]([O:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[O:12])=[CH:24][CH:25]=1)#[N:30]

Participants

7

Reactant 3

HCID 3283Diethyl EtherHCID 14798Sodium HydroxideHCID 88118165(1R)-2-{[(Benzyloxy)carbonyl]amino}-1-[(4-cyanophenoxy)methyl]ethyl Methanesulfonate

Product 1

HCID 90843497Benzyl (2s)-2-[(4-cyanophenoxy)methyl]-1-aziridinecarboxylateYield 69%

Reagents, catalysts & solvents 3

HCID 94433Tetrabutylammonium hydrogen sulfateCatalystHCID 962WaterSolvent2×HCID 6344DichloromethaneSolvent

Procedure

A solution of NaOH in water (11 mL of 50 wt. %) was added under vigorous stirring to a solution of (1R)-2-{[(benzyloxy)carbonyl]amino}-1-[(4-cyanophenoxy)-methyl]ethyl methanesulfonate (see step (iv) above; 5.7 g, 14.1 mmol) and tetrabutylammonium hydrogensulfate (0.6 g, 1.7 mmol) in DCM (34 mL). The mixture was stirred for 1 h before water (200 mL) and ether (200 mL) were added. The organic phase was washed with water and then dried. The solvents were evaporated and the resulting residue was purified by chromatography (DCM eluant) to yield 3.0 g (69%) of the sub-title compound.

Workup

  1. additionwere added
  2. washThe organic phase was washed with water
  3. customdried
  4. customThe solvents were evaporated
  5. customthe resulting residue was purified by chromatography (DCM eluant)

Sources & evidence

ORD record
ord-43e786769e104bee825856b26c727f52
Source dataset
uspto-grants-2003_05
Patent number
US06559162B2

Reaction notes

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