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

HRID 704776ノート

反応式

HRID 704776 の反応式
[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

参加物

5

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 312751,4-Dioxane溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-602ec3827b6642d982cfd269fadfc365
出典データセット
uspto-grants-1991_01
特許番号
US04988723

反応ノート

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