Sodium hydride → (Z)-((2R,4R,6R)-2-Methoxy-2-((R)-3-(4-methoxybenzyl)-2-oxothiazolidin-4-yl)-6-(pent-4-enyl)-tetrahydro-2H-pyran-4-yl) 3-Methylhepta-2,6-dienoate

HRID 1445378ノート

反応式

HRID 1445378 の反応式
[H-].[Na+].[CH3:3]/[C:4](/[CH2:9][CH2:10][CH:11]=[CH2:12])=[CH:5]/[C:6]([OH:8])=[O:7].C1OCCOCCOCCOCCOC1.FC(F)(F)S(O[C@H:34]1[CH2:39][C@@H:38]([CH2:40][CH2:41][CH2:42][CH:43]=[CH2:44])[O:37][C@@:36]([O:60][CH3:61])([C@@H:45]2[CH2:49][S:48][C:47](=[O:50])[N:46]2[CH2:51][C:52]2[CH:57]=[CH:56][C:55]([O:58][CH3:59])=[CH:54][CH:53]=2)[CH2:35]1)(=O)=O>C1COCC1>[CH3:3]/[C:4](/[CH2:9][CH2:10][CH:11]=[CH2:12])=[CH:5]/[C:6]([O:8][C@@H:34]1[CH2:39][C@@H:38]([CH2:40][CH2:41][CH2:42][CH:43]=[CH2:44])[O:37][C@@:36]([O:60][CH3:61])([C@@H:45]2[CH2:49][S:48][C:47](=[O:50])[N:46]2[CH2:51][C:52]2[CH:53]=[CH:54][C:55]([O:58][CH3:59])=[CH:56][CH:57]=2)[CH2:35]1)=[O:7]

参加物

6

反応物 4

HCID 24758Sodium hydrideHCID 3633615-Crown-5HCID 13947388(2Z)-3-Methylhepta-2,6-dienoic acidHCID 59644094(2R,4S,6R)-2-Methoxy-2-((R)-3-(4-methoxybenzyl)-2-oxothiazolidin-4-yl)-6-(pent-4-enyl)-tetrahydro-2H-pyran-4-yl Trifluoromethanesulfonate

生成物 1

HCID 59644056(Z)-((2R,4R,6R)-2-Methoxy-2-((R)-3-(4-methoxybenzyl)-2-oxothiazolidin-4-yl)-6-(pent-4-enyl)-tetrahydro-2H-pyran-4-yl) 3-Methylhepta-2,6-dienoate

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
0 °C

実験手順

A 100 mL dry flask under a nitrogen atmosphere was charged with NaH (60% in mineral oil, 186 mg, 4.65 mmol). The NaH was washed with pentane (5 mL), THF (2 mL) was added, and the reaction was cooled to 0° C. The title compound from Example 21 (651 mg, 4.65 mmol) in THF (3 mL) was added dropwise, after which 15-crown-5 (1.41 mL, 7.12 mmol) was added. The reaction was allowed to warm to room temperature and stirred for 10 minutes, and then was cooled to 0° C. again. A solution of the title compound from Example 22 (1.19 mmol, used directly from the previous reaction) in THF (2 mL) was added, and the reaction was stirred at room temperature overnight.

後処理

  1. customA 100 mL dry flask under a nitrogen atmosphere
  2. washThe NaH was washed with pentane (5 mL), THF (2 mL)
  3. additionwas added
  4. temperatureto warm to room temperature
  5. temperaturewas cooled to 0° C. again
  6. additionwas added
  7. stirringthe reaction was stirred at room temperature overnight

出典と根拠

ORDレコード
ord-131c7a36ca54476eb8e0764b685d6dd9
出典データセット
uspto-grants-2010_02
特許番号
US07666861B2

反応ノート

読み込み中…