Allyl Alcohol → HCID 89444286, compound

HRID 593207Notes

Reaction equation

HRID 593207 reaction equation
[CH2:1](O)[CH:2]=[CH2:3].S(Cl)(Cl)=O.[Cl:9][C:10]1[N:11]=[CH:12][C:13]([NH:16][C:17](=[O:23])[CH2:18][CH2:19][C:20]([OH:22])=[O:21])=[N:14][CH:15]=1>>[Cl:9][C:10]1[N:11]=[CH:12][C:13]([NH:16][C:17](=[O:23])[CH2:18][CH2:19][C:20]([O:22][CH2:3][CH:2]=[CH2:1])=[O:21])=[N:14][CH:15]=1

Participants

4

Reactant 3

HCID 7858Allyl AlcoholHCID 24386Thionyl ChlorideHCID 89444401HCID 89444401, compound

Product 1

HCID 89444286HCID 89444286, compound

Procedure

To a solution of prop-2-en-1-ol (2 mL) was added dropwise thionyl chloride (3 eq, 1.7 mmol). After 5 min, 4-[(5-chloropyrazin-2-yl)amino]-4-oxo-butanoic acid A6 (prepared as described before, 0.13 g, 0.57 mmol) was added to the solution. The reaction mixture was stirred overnight at room temperature. The reaction was stopped and the solution was partitioned between ethyl acetate and water. The aqueous layer was separated and extracted with ethyl acetate (2×). The combined organic layer was washed with a saturated solution of sodium hydrogenocarbonete and dried on magnesium sulfate, then concentrated under vacuum. The residue was first washed with cyclohexane and the solid obtained was purified by flash chromatography eluting with cyclohexane-ethyl acetate to give allyl 4-[(5-chloropyrazin-2-yl)amino]-4-oxo-butanoate A10 (37%). 1H NMR (400 MHz, CDCl3) 9.29 (s, 1H), 8.27 (s, 1H), 8.18 (bs, 1H), 5.92 (m, 1H), 5.29 (m, 2H), 4.62 (m, 2H), 2.80 (m, 4H).

Workup

  1. customthe solution was partitioned between ethyl acetate and water
  2. customThe aqueous layer was separated
  3. extractionextracted with ethyl acetate (2×)
  4. washThe combined organic layer was washed with a saturated solution of sodium hydrogenocarbonete
  5. customdried on magnesium sulfate
  6. concentrationconcentrated under vacuum
  7. washThe residue was first washed with cyclohexane
  8. customthe solid obtained
  9. customwas purified by flash chromatography
  10. washeluting with cyclohexane-ethyl acetate

Sources & evidence

ORD record
ord-2d7a88e2cbe446fb898a5df06ef8dc90
Source dataset
uspto-grants-2016_01
Patent number
US09241489B2

Reaction notes

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