Pyridine → HCID 25119929, compound

HRID 1966941Notes

Reaction equation

HRID 1966941 reaction equation
N1[CH2:7][C:5](=[O:6])[NH:4][C:2]1=[O:3].[NH2:8][C@H:9]([C:12]([OH:14])=O)[CH2:10][OH:11].N1C=CC=CC=1.[C:21](Cl)(=[O:23])[CH3:22].[CH3:25][C:26]([O:29]C)(C)C>CC#N>[C:21]([C:9]1([CH2:10][OH:11])[N:8]([C:26](=[O:29])[CH3:25])[C:2](=[O:3])[N:4]([C:5](=[O:6])[CH3:7])[C:12]1=[O:14])(=[O:23])[CH3:22]

Participants

6

Reactant 4

HCID 1049PyridineHCID 6367Acetyl chlorideHCID 15413tert-Butyl methyl etherHCID 66819706HCID 66819706, compound

Product 1

HCID 25119929HCID 25119929, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
10 °C

Procedure

L-Serine hydantoin (41.4 g, 318 mmol) was suspended in dry MeCN (330 mL) and the solution was cooled to 10° C. Pyridine (88.3 g, 1.11 mol) was added followed by drop wise addition during approx. 1 h of acetyl chloride (87.4 g, 1.11 mol), such that the temperature was maintained at 10° C. After the addition, the reaction was allowed to warm up to 20° C. while a precipitate formed that gradually dissolved. After approx. 16 h, the reaction was complete (as determined by 1H NMR in CDCl3) and was concentrated on the rotavapor at 40° C. to a weight of approx. 240 g during which some solids formed. MTBE (500 mL) was added and more solid precipitated. After stirring for 10 min, the precipitate was collected on a funnel via suction. The cake was washed with additional MTBE (100 mL) and then discarded. The title product resided in the mother liquor. This was concentrated on a rotavapor at 40° C. to thick oil. Weight 73.0 g, ca. 95% purity, approx. 85% yield. 1H NMR: (CDCl3, 300 MHz): δ 4.83 (dd, 1H), 4.73 (t, 1H), 4.44 (dd, 1H), 2.61 (s, 3H), 2.60 (s, 3H), 2.03 (s, 3H).

Workup

  1. temperaturewas maintained at 10° C
  2. additionAfter the addition
  3. temperatureto warm up to 20° C. while a precipitate
  4. customformed
  5. dissolutionthat gradually dissolved
  6. concentrationwas concentrated on the rotavapor at 40° C. to a weight of approx. 240 g during which some solids
  7. customformed
  8. custommore solid precipitated
  9. customthe precipitate was collected on a funnel via suction
  10. washThe cake was washed with additional MTBE (100 mL)
  11. concentrationThis was concentrated on a rotavapor at 40° C. to thick oil

Sources & evidence

ORD record
ord-aec4012502e24caaa9ef2e6c6f2f335a
Source dataset
uspto-grants-2013_04
Patent number
US08420683B2

Reaction notes

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