Sodium Hydroxide → (1aS,7bS)-2,2-Dimethyl-1a,7b-dihydro-2H-oxireno[2,3-c]chromene-6-carbonitrile

HRID 704776

반응식

HRID 704776 반응식
[OH-].[Na+].C(OC(N[C@@H](C)C([O:17][C@H:18]1[C:23]2[CH:24]=[C:25]([C:28]#[N:29])[CH:26]=[CH:27][C:22]=2[O:21][C:20]([CH3:31])([CH3:30])[C@@H:19]1Br)=O)=O)C1C=CC=CC=1>O.O1CCOCC1>[O:17]1[C@@H:18]2[C@H:19]1[C:20]([CH3:30])([CH3:31])[O:21][C:22]1[CH:27]=[CH:26][C:25]([C:28]#[N:29])=[CH:24][C:23]=12

참가 물질

5

반응물 2

HCID 14798Sodium HydroxideHCID 18643511(3R,4S)-4-{(2S)-2-benzyloxycarbonylaminopropionyloxy}-3-bromo-3,4-dihydro-2,2-dimethyl-2H-1-benzopyran-6-carbonitrile

생성물 1

HCID 9837089(1aS,7bS)-2,2-Dimethyl-1a,7b-dihydro-2H-oxireno[2,3-c]chromene-6-carbonitrile수율 87.1%

시약·촉매·용매 2

HCID 962Water용매HCID 312751,4-Dioxane용매

실험 절차

A solution of sodium hydroxide (0.672 g) in water (16 ml) was added dropwise to a stirred solution of (3R,4S)-4-{(2S)-2-benzyloxycarbonylaminopropionyloxy}-3-bromo-3,4-dihydro-2,2-dimethyl-2H-1-benzopyran-6-carbonitrile (3.896 g) in 1,4-dioxane (24 ml). After being stirred at ambient temperature for 1 hour, the mixture was poured into ice-water and extracted with ethyl acetate. The extract was washed with water, dried over magnesium sulfate, and evaporated in vacuo. The crystalline residue was washed with isopropyl ether and dried to give (3S,4S)-3,4-epoxy-3,4-dihydro-2,2-dimethyl-2H-1-benzopyran-6-carbonitrile (1.401 g).

후처리

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed with water
  3. dry with materialdried over magnesium sulfate
  4. customevaporated in vacuo
  5. washThe crystalline residue was washed with isopropyl ether
  6. customdried

출처 및 근거

ORD 기록
ord-602ec3827b6642d982cfd269fadfc365
출처 데이터셋
uspto-grants-1991_01
특허 번호
US04988723

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