Sodium hydride → HCID 58109548, compound

HRID 2037615Notes

Reaction equation

HRID 2037615 reaction equation
[O:1]1[CH2:6][CH2:5][CH2:4][O:3][CH:2]1[C:7]1[CH:12]=[CH:11][C:10]([C:13]([OH:35])([CH3:34])[CH2:14][CH2:15][N:16]([C@H:24]([C:26]2[CH:31]=[CH:30][C:29]([O:32][CH3:33])=[CH:28][CH:27]=2)[CH3:25])[C:17](=O)[O:18]C(C)(C)C)=[CH:9][CH:8]=1.[H-].[Na+]>C1COCC1>[O:1]1[CH2:6][CH2:5][CH2:4][O:3][CH:2]1[C:7]1[CH:8]=[CH:9][C:10]([C:13]2([CH3:34])[O:35][C:17](=[O:18])[N:16]([C@H:24]([C:26]3[CH:31]=[CH:30][C:29]([O:32][CH3:33])=[CH:28][CH:27]=3)[CH3:25])[CH2:15][CH2:14]2)=[CH:11][CH:12]=1

Participants

4

Reactant 2

HCID 24758Sodium hydrideHCID 58109405HCID 58109405, compound

Product 1

HCID 58109548HCID 58109548, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of tert-butyl 3-(4-(1,3-dioxan-2-yl)phenyl)-3-hydroxybutyl((S)-1-(4-methoxyphenyl)ethyl)carbamate, obtained as described above, and 1.340 g of 60% NaH in THF (10 mL) was heated to reflux for 24 h. The reaction was then quenched with 1.5 mL of H2O, diluted with CH2Cl2, dried over Na2SO4. Removal of the solvent afforded crude 6-(4-(1,3-dioxan-2-yl)phenyl)-3-((S)-1-(4-methoxyphenyl)ethyl)-6-methyl-1,3-oxazinan-2-one. LC-MS Method 1 tR=1.65, 1.69 min, m/z=412 (MH+).

Workup

  1. customobtained
  2. temperaturewas heated
  3. temperatureto reflux for 24 h
  4. customThe reaction was then quenched with 1.5 mL of H2O
  5. additiondiluted with CH2Cl2
  6. dry with materialdried over Na2SO4
  7. customRemoval of the solvent

Sources & evidence

ORD record
ord-26164364a0b342d6a608cd19c3e96997
Source dataset
uspto-grants-2013_11
Patent number
US08575156B2

Reaction notes

Loading…