Methanol → HCID 68720410, compound

HRID 885107Notes

Reaction equation

HRID 885107 reaction equation
[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([C:10]2[S:14][C:13]([C:15]3([OH:21])[CH2:20][CH2:19][O:18][CH2:17][CH2:16]3)=[N:12][CH:11]=2)=[N:8][CH:9]=1)([O-])=O.CO>[Zn].C(O)(=O)C>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]([C:10]2[S:14][C:13]([C:15]3([OH:21])[CH2:16][CH2:17][O:18][CH2:19][CH2:20]3)=[N:12][CH:11]=2)=[N:8][CH:9]=1

Participants

5

Reactant 2

HCID 887MethanolHCID 68720433HCID 68720433, compound

Product 1

HCID 68720410HCID 68720410, compound

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 176Acetic AcidSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of Example 7A (0.106 g, 0.344 mmol) in a solvent mixture of methanol (2 mL) and acetic acid (2 mL) was added Zn powder (0.067 g, 1.03 mmol). The reaction was heated to 50° C. for 5 h, and was then cooled to room temperature. The reaction was quenched by the addition of saturated aqueous NaHCO3 (5 mL) and ethyl acetate (5 mL). The layers were separated, and the aqueous was extracted with additional ethyl acetate (2×5 mL). The combined organics were dried with anhydrous Na2SO4, filtered, and concentrated under reduced pressure to yield the title compound, which was used without further purification. MS (ESI) m/z 278 [M+H]+.

Workup

  1. temperaturewas then cooled to room temperature
  2. customThe reaction was quenched by the addition of saturated aqueous NaHCO3 (5 mL) and ethyl acetate (5 mL)
  3. customThe layers were separated
  4. extractionthe aqueous was extracted with additional ethyl acetate (2×5 mL)
  5. dry with materialThe combined organics were dried with anhydrous Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-46952eb451b942cc9509787e9a9b1ad4
Source dataset
uspto-grants-2012_08
Patent number
US08242139B2

Reaction notes

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