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 2251767노트

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HRID 2251767 반응식
[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>[CH3:61][O:60][C@:36]1([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][C@H:34]([O:7][C:6](=[O:8])/[CH:5]=[C:4](/[CH3:3])\[CH2:9][CH2:10][CH:11]=[CH2:12])[CH2:39][C@@H:38]([CH2:40][CH2:41][CH2:42][CH:43]=[CH2:44])[O:37]1

참가 물질

6

반응물 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

생성물 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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

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온도
0 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-515c5a0df41a4235bd8793d0b24c15a6
출처 데이터셋
uspto-grants-2008_01
특허 번호
US07320974B2

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