Trimethyl orthoformate → methyl 4-[(3aR,4R,6R,6aR)-6-(hydroxymethyl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl]-3-oxo-3,4-dihydro-2-pyrazinecarboxylate

HRID 392309ノート

反応式

HRID 392309 の反応式
[OH:1][C@@H:2]1[C@H:6]([OH:7])[C@@H:5]([CH2:8][OH:9])[O:4][C@H:3]1[N:10]1[CH:15]=[CH:14][N:13]=[C:12]([C:16]([O:18][CH3:19])=[O:17])[C:11]1=[O:20].C(OC)(OC)OC.O.[C:29]1(C)[CH:34]=CC(S(O)(=O)=O)=C[CH:30]=1>CC(C)=O>[OH:9][CH2:8][C@@H:5]1[C@H:6]2[O:7][C:29]([CH3:34])([CH3:30])[O:1][C@H:2]2[C@H:3]([N:10]2[CH:15]=[CH:14][N:13]=[C:12]([C:16]([O:18][CH3:19])=[O:17])[C:11]2=[O:20])[O:4]1

参加物

5

反応物 3

HCID 9005Trimethyl orthoformateHCID 521998p-Toluenesulfonic acid monohydrateHCID 11492964methyl 4-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydro-2-furanyl]-3-oxo-3,4-dihydro-2-pyrazinecarboxylate

生成物 1

HCID 60126642methyl 4-[(3aR,4R,6R,6aR)-6-(hydroxymethyl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl]-3-oxo-3,4-dihydro-2-pyrazinecarboxylate収率 865.6%

試薬・触媒・溶媒 1

HCID 180Acetone溶媒

実験手順

In 5 mL of acetone was suspended 0.50 g of methyl 4-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydro-2-furanyl]-3-oxo-3,4-dihydro-2-pyrazinecarboxylate. Then, 1 ml of trimethyl orthoformate and 33 mg of p-toluenesulfonic acid monohydrate were successively added, the mixture thus obtained was heated under reflux for one hour, and the solvent was removed under reduced pressure. By purifying the residue by column chromatography [eluent: ethyl acetate], 0.49 g of methyl 4-[(3aR,4R,6R,6aR)-6-(hydroxymethyl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl]-3-oxo-3,4-dihydro-2-pyrazinecarboxylate was obtained as a white-colored solid product.

後処理

  1. customthe mixture thus obtained
  2. temperaturewas heated
  3. temperatureunder reflux for one hour
  4. customthe solvent was removed under reduced pressure
  5. customBy purifying the residue by column chromatography [eluent: ethyl acetate]

出典と根拠

ORDレコード
ord-ed4aafc81f2547beaab02ae600a94142
出典データセット
uspto-grants-2004_10
特許番号
US06800629B2

反応ノート

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