Sodium Sulfate → HCID 58380829, compound

HRID 1948152Notes

Reaction equation

HRID 1948152 reaction equation
[CH2:1]([C:3]1([CH:13]=[N:14][S:15]([C:17]([CH3:20])([CH3:19])[CH3:18])=[O:16])[CH2:12][CH2:11][C:6]2([O:10][CH2:9][CH2:8][O:7]2)[CH2:5][CH2:4]1)[CH3:2].[CH2:21](C1(C#N)CCC2(OCCO2)CC1)[CH3:22].C1(CC2(C=NS(C(C)(C)C)=O)CCC3(OCCO3)CC2)CC1.C([Mg]Br)=C.S([O-])([O-])(=O)=O.[Na+].[Na+]>O1CCCC1>[CH2:1]([C:3]1([CH:13]([NH:14][S:15]([C:17]([CH3:19])([CH3:18])[CH3:20])=[O:16])[CH:21]=[CH2:22])[CH2:4][CH2:5][C:6]2([O:7][CH2:8][CH2:9][O:10]2)[CH2:11][CH2:12]1)[CH3:2]

Participants

7

Reactant 5

HCID 24436Sodium SulfateHCID 67072565HCID 67072565, compoundHCID 67072577HCID 67072577, compoundHCID 67072583HCID 67072583, compoundHCID 178418507HCID 178418507, compound2×

Product 1

HCID 58380829HCID 58380829, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Under argon, 2.00 g (6.64 mmol) of 2-methyl-propane-2-sulfinic acid 1-(8-ethyl-1,4-dioxa-spiro[4.5]dec-8-yl)-methylideneamide (prepared from 8-ethyl-1,4-dioxa-spiro[4.5]decane-8-carbonitrile using the protocol described for the synthesis of 19) were dissolved in 5 mL of absolute tetrahydrofuran. Then, 7.30 mL (7.30 mmol) of vinylmagnesium bromide (1M in tetrahydrofuran) were added dropwise at 0° C. and the reaction mixture was stirred for 17 h at room temperature. Another 16.6 mL (16.6 mmol) of vinylmagnesium bromide (1M in tetrahydrofuran) were added and the mixture stirred for 2 h at room temperature. The reaction mixture was cooled to 0° C. and 15 mL of saturated aqueous sodium sulphate solution were added. The suspension was filtered over celite, the organic layer was dried over magnesium sulphate, filtered, and concentrated in vacuo. The crude product was purified by flash chromatography (SiO2, 0%→100% ethyl acetate in heptane) to yield 1.30 g of the title compound 57 as mixture of diastereoisomers. Rt=2.19, 2.26 min (Method N). Detected mass: 330.2 (M+H+).

Workup

  1. stirringthe mixture stirred for 2 h at room temperature
  2. temperatureThe reaction mixture was cooled to 0° C.
  3. filtrationThe suspension was filtered over celite
  4. dry with materialthe organic layer was dried over magnesium sulphate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe crude product was purified by flash chromatography (SiO2, 0%→100% ethyl acetate in heptane)

Sources & evidence

ORD record
ord-88864879cecc42c29ac830ca78a3e5ce
Source dataset
uspto-grants-2013_03
Patent number
US08399482B2

Reaction notes

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