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

HRID 411543
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HRID 411543 반응식
[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]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 3

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

생성물 1

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

시약·촉매·용매 3

HCID 94433Tetrabutylammonium hydrogen sulfate촉매
HCID 962Water용매2회
HCID 6344Dichloromethane용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-43e786769e104bee825856b26c727f52
출처 데이터셋
uspto-grants-2003_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06559162B2

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