Potassium Bromide → tert-Butyl 3,5-dideoxy-2,4-O-(1-methylethylidene)-L-erythro-hexuronate

HRID 877954ノート

反応式

HRID 877954 の反応式
C1C2CC3N([O])C(C2)CC1C3.[Br-].[K+].[OH:14][CH2:15][C@H:16]1[O:21][C:20]([CH3:23])([CH3:22])[O:19][C@@H:18]([CH2:24][C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH2:17]1.Cl[O-].[Na+]>C(Cl)Cl>[CH:15]([C@H:16]1[O:21][C:20]([CH3:23])([CH3:22])[O:19][C@@H:18]([CH2:24][C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH2:17]1)=[O:14]

参加物

6

反応物 4

HCID 253877Potassium BromideHCID 9816650tert-Butyl 2,4-dideoxy-3,5-O-(1-methylethylidene)-D-erythro-hexonateHCID 23665760Sodium HypochloriteHCID 42643072(2-Azatricyclo[3.3.1.1~3,7~]decan-2-yl)oxidanyl

生成物 1

HCID 9881588tert-Butyl 3,5-dideoxy-2,4-O-(1-methylethylidene)-L-erythro-hexuronate

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To the −15° C. to −5° C. pre-cooled reaction mixture of AZADO (0.002 g), potassium bromide (0.22 g) and methylene chloride (30 ml) added 5 g of tert-butyl 2-((4R,6S)-6-(hydroxymethyl)-2,2-dimethyl-1,3-dioxan-4-yl)acetate. Stirred the reaction mixture for 15 minutes at −15° C. to −5° C. 19 ml of sodium hypochlorite solution was added to the reaction mixture at same temperature. Stirred the reaction mixture for 15 minutes. Quenched the reaction mixture with 10% aqueous sodium thiosulfate solution. 20 ml of water was added and separated the both aqueous and organic layers. Washed the organic layer with water followed by brine solution. Distilled off the solvent completely to get the title compound as a solid.

後処理

  1. temperatureTo the −15° C. to −5° C. pre-cooled
  2. stirringStirred the reaction mixture for 15 minutes
  3. customQuenched the reaction mixture with 10% aqueous sodium thiosulfate solution
  4. addition20 ml of water was added
  5. customseparated the both aqueous and organic layers
  6. washWashed the organic layer with water
  7. distillationDistilled off the solvent completely

出典と根拠

ORDレコード
ord-38cfc2d0ed21467189403a902cbdd5ae
出典データセット
uspto-grants-2015_03
特許番号
US08987444B2

反応ノート

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