Sodium methanethiolate → HCID 67287391、化合物

HRID 46197ノート

反応式

HRID 46197 の反応式
Cl[C:2]1[S:3][C:4]([CH2:7][C:8]2[CH:13]=[C:12]([C@H:14]3[C@H:19]([O:20][CH2:21][C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=4)[C@@H:18]([O:28][CH2:29][C:30]4[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=4)[C@H:17]([O:36][CH2:37][C:38]4[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=4)[C@@H:16]([CH2:44][O:45][CH2:46][C:47]4[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=4)[O:15]3)[CH:11]=[CH:10][C:9]=2[Cl:53])=[N:5][N:6]=1.[CH3:54][S-:55].[Na+]>O1CCCC1>[Cl:53][C:9]1[CH:10]=[CH:11][C:12]([C@H:14]2[C@H:19]([O:20][CH2:21][C:22]3[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=3)[C@@H:18]([O:28][CH2:29][C:30]3[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=3)[C@H:17]([O:36][CH2:37][C:38]3[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=3)[C@@H:16]([CH2:44][O:45][CH2:46][C:47]3[CH:48]=[CH:49][CH:50]=[CH:51][CH:52]=3)[O:15]2)=[CH:13][C:8]=1[CH2:7][C:4]1[S:3][C:2]([S:55][CH3:54])=[N:6][N:5]=1

参加物

4

反応物 2

HCID 4378561Sodium methanethiolateHCID 672869552-Chloro-5-(2-chloro-5-((2S,3S,4R,5R,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)-tetrahydro-2H-pyran-2-yl)benzyl)-1,3,4-thiadiazole

生成物 1

HCID 67287391HCID 67287391、化合物収率 77%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of 2-chloro-5-(2-chloro-5-((2S,3S,4R,5R,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)-tetrahydro-2H-pyran-2-yl)benzyl)-1,3,4-thiadiazole (419 mg, 0.55 mmol) from Step 2 in tetrahydrofuran (10 mL) was added sodium methanethiolate (77 mg, 1.1 mmol). The resulting mixture was stirred at ambient temperature overnight. After cooling to 0° C., the reaction was quenched with hydrochloric acid (1.0 M) and diluted with ethyl acetate and water. The organic layer was separated and the aqueous layer was extracted with ethyl acetate. The combined organic layers were washed with brine, dried over magnesium sulfate, filtered and concentrated in vacuo. The residue was purified on Biotage® purification apparatus (silica gel, 10 to 60% ethyl acetate in hexanes) to yield the title compound (331 mg, 0.42 mmol, 77%) as a yellow oil. MH+ 779.

後処理

  1. temperatureAfter cooling to 0° C.
  2. customthe reaction was quenched with hydrochloric acid (1.0 M)
  3. additiondiluted with ethyl acetate and water
  4. customThe organic layer was separated
  5. extractionthe aqueous layer was extracted with ethyl acetate
  6. washThe combined organic layers were washed with brine
  7. dry with materialdried over magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. customThe residue was purified on Biotage® purification apparatus (silica gel, 10 to 60% ethyl acetate in hexanes)

出典と根拠

ORDレコード
ord-1b8032a7eb284b2a98884ad809915433
出典データセット
uspto-grants-2013_09
特許番号
US08541380B2

反応ノート

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