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 1664255Notes

Reaction equation

HRID 1664255 reaction equation
[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]

Participants

6

Reactant 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

Product 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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-a184f9861c2e471eb55bee9954094717
Source dataset
uspto-grants-2011_10
Patent number
US08039465B2

Reaction notes

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