Dimethyl Sulfide → HCID 86689165, compound

HRID 1752486Notes

Reaction equation

HRID 1752486 reaction equation
[CH3:1][O:2][C:3]([C:5]1[C:10]([N:11]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])=[N:9][C:8]([CH:26]=C)=[CH:7][N:6]=1)=[O:4].C(=O)(O)[O-:29].[Na+].CSC>C(Cl)Cl.CO>[CH3:1][O:2][C:3]([C:5]1[C:10]([N:11]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[C:12]([O:14][C:15]([CH3:16])([CH3:18])[CH3:17])=[O:13])=[N:9][C:8]([CH:26]=[O:29])=[CH:7][N:6]=1)=[O:4]

Participants

6

Reactant 3

HCID 1068Dimethyl SulfideHCID 516892Sodium BicarbonateHCID 68109953HCID 68109953, compound

Product 1

HCID 86689165HCID 86689165, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent2×

Conditions

Temperature
-78 °C

Procedure

A mixture of 3-(di-tert-butoxycarbonyl-amino)-5-vinyl-pyrazine-2-carboxylic acid methyl ester (1 g, 2.64 mmol) and sodium bicarbonate (0.332 g, 3.95 mmol) in DCM (45 ml) and MeOH (15 ml) was cooled to −78° C. and purged with oxygen for 5 min. The reaction mixture was treated with ozone for 40 min until the mixture turned blue. The reaction mixture was purged with oxygen for 10 min and with nitrogen for 10 min, then dimethyl sulfide (0.487 ml, 6.59 mmol) was added at −78° C. and the mixture was allowed to warm to room temperature. The mixture was diluted with DCM and washed with 10% aq. sodium thiosulfate. The aq. layer was extracted with DCM and the combined organic layers were dried with Na2SO4 and evaporated to provide the title compound as yellow oil. The compound was used for the next step without further purification.

Workup

  1. custompurged with oxygen for 5 min
  2. additionThe reaction mixture was treated with ozone for 40 min until the mixture
  3. customThe reaction mixture was purged with oxygen for 10 min and with nitrogen for 10 min
  4. temperatureto warm to room temperature
  5. washwashed with 10% aq. sodium thiosulfate
  6. extractionThe aq. layer was extracted with DCM
  7. dry with materialthe combined organic layers were dried with Na2SO4
  8. customevaporated

Sources & evidence

ORD record
ord-c331c8f934294f54be23be09ac50e19b
Source dataset
uspto-grants-2015_10
Patent number
US09163011B2

Reaction notes

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