Sodium hydride → HCID 131734320, compound

HRID 1504029Notes

Reaction equation

HRID 1504029 reaction equation
[O:1]1[C:5]2([CH2:10][CH2:9][CH:8]([OH:11])[CH2:7][CH2:6]2)[O:4][CH2:3][CH2:2]1.[H-].[Na+].[Si:14]([O:21][CH2:22][C@H:23]1[CH2:34][CH2:33][C:32]2[S:31][C:30]3[N:29]=[CH:28][N:27]=[C:26](Cl)[C:25]=3[C:24]1=2)([C:17]([CH3:20])([CH3:19])[CH3:18])([CH3:16])[CH3:15]>C1COCC1>[Si:14]([O:21][CH2:22][C@H:23]1[CH2:34][CH2:33][C:32]2[S:31][C:30]3[N:29]=[CH:28][N:27]=[C:26]([O:11][CH:8]4[CH2:9][CH2:10][C:5]5([O:4][CH2:3][CH2:2][O:1]5)[CH2:6][CH2:7]4)[C:25]=3[C:24]1=2)([C:17]([CH3:20])([CH3:18])[CH3:19])([CH3:16])[CH3:15]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 5673521,4-Dioxaspiro(4.5)decan-8-olHCID 86695146HCID 86695146, compound

Product 1

HCID 131734320HCID 131734320, compoundYield 88.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 1,4-dioxaspiro[4.5]decan-8-ol (379 mg, 2.40 mmol, 1.20 equiv) in freshly distilled THF (10 mL) was added sodium hydride (60% dispersion in mineral oil, 320 mg, 8.00 mmol, 4.00 equiv) in ice/water bath and stirred for 30 min under nitrogen. A solution of (3S)-3-[[(tert-butyldimethylsilyl)oxy]methyl]-12-chloro-7-thia-9,11-diazatricyclo[6.4.0.0[2,6]]dodeca-1(8),2(6),9,11-tetraene (710 mg, 2.00 mmol, 1.00 equiv) in 10 mL of anhydrous THF was added dropwise and the resulting solution was stirred for 3 h at 60° C. After cooling, the mixture was then quenched with water, extracted with EtOAc (100 mL), dried over anhydrous sodium sulfate. The solvents were evaporated under reduced pressure to obtain (3S)-3-[[(tert-butyldimethylsilyl)oxy]methyl]-12-[1,4-dioxaspiro[4.5]decan-8-yloxy]-7-thia-9,11-diazatricyclo[6.4.0.0[2,6]]dodeca-1(8),2(6),9,11-tetraene (840 mg, 88%) as a yellow oil.

Workup

  1. stirringthe resulting solution was stirred for 3 h at 60° C
  2. temperatureAfter cooling
  3. customthe mixture was then quenched with water
  4. extractionextracted with EtOAc (100 mL)
  5. dry with materialdried over anhydrous sodium sulfate
  6. customThe solvents were evaporated under reduced pressure

Sources & evidence

ORD record
ord-9eb7227e37f94fbcae7d366170f61120
Source dataset
uspto-grants-2015_12
Patent number
US09212190B2

Reaction notes

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