Potassium Fluoride → HCID 66608418、化合物

HRID 220998

反応式

HRID 220998 の反応式
Br[CH2:2][C:3]1[N:4]=[N:5][N:6]([C@@H:8]2[O:25][C@H:24]([CH2:26][O:27][C:28](=[O:30])[CH3:29])[C@@H:19]([O:20][C:21](=[O:23])[CH3:22])[C@H:14]([O:15][C:16](=[O:18])[CH3:17])[C@H:9]2[O:10][C:11](=[O:13])[CH3:12])[CH:7]=1.C([Sn](CCCC)(CCCC)[C:36]1[CH:41]=[CH:40][C:39]([CH2:42][CH3:43])=[CH:38][CH:37]=1)CCC.[F-].[K+]>O1CCCC1.C(OCC)(=O)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH2:42]([C:39]1[CH:40]=[CH:41][C:36]([CH2:2][C:3]2[N:4]=[N:5][N:6]([C@@H:8]3[O:25][C@H:24]([CH2:26][O:27][C:28](=[O:30])[CH3:29])[C@@H:19]([O:20][C:21](=[O:23])[CH3:22])[C@H:14]([O:15][C:16](=[O:18])[CH3:17])[C@H:9]3[O:10][C:11](=[O:13])[CH3:12])[CH:7]=2)=[CH:37][CH:38]=1)[CH3:43]

参加物

7

反応物 3

HCID 522689Potassium FluorideHCID 60041267Tributyl-(4-ethylphenyl)stannaneHCID 666083074-(bromomethyl)-1-(2,3,4,6-tetra-O-acetyl-beta-D-glucopyranosyl)-1,2,3-triazole

生成物 1

HCID 66608418HCID 66608418、化合物収率 17.1%

試薬・触媒・溶媒 3

HCID 178418397HCID 178418397、化合物触媒HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
70 °C

実験手順

A solution of 4-(bromomethyl)-1-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-1,2,3-triazole 32 (500 mg) (See Federico G. H. et al., J. Med. Chem. (1979) 29, 496), tri-n-butyl(4-ethylphenyl)tin 33 (604 mg) and tetrakis(triphenylphosphine)palladium (0) (59 mg) in tetrahydrofuran (10 ml) was stirred under heating at 70° C. for 12 hours under argon atmosphere. The reaction mixture was cooled to room temperature, diluted with ethyl acetate, and then, an aqueous potassium fluoride solution was added thereto and the mixture was stirred at room temperature for one hour. Insoluble materials were filtered off, and the filtrate was washed with water, and dried over magnesium sulfate. The solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=90:10-50:50) to give 4-(4-ethylphenylmethyl)-1-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-1,2,3-triazole 34 (90 mg) as a colorless solid. APCI-Mass m/Z 518 (M+H). (2) From the above tetraacetate compound 34, the desired 4-(4-ethylphenylmethyl)-1-(β-D-glucopyranosyl)1,2,3-triazole 35 was prepared in a manner similar to Example 106-(3) as a colorless solid.

後処理

  1. temperatureThe reaction mixture was cooled to room temperature
  2. filtrationInsoluble materials were filtered off
  3. washthe filtrate was washed with water
  4. dry with materialdried over magnesium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=90:10-50:50)

出典と根拠

ORDレコード
ord-cbb99d5359134467ac8861c81d205ae6
出典データセット
uspto-grants-2012_06
特許番号
US08202984B2

関連ノート

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