HCID 69641948, compound → HCID 22247808, compound

HRID 889856Notes

Reaction equation

HRID 889856 reaction equation
C1(C[O:8][C:9](=[O:22])[CH2:10][C:11](=[O:21])[NH:12][CH2:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][N:16]=2)C=CC=CC=1>C1COCC1.[Pd]>[O:21]=[C:11]([NH:12][CH2:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][N:16]=1)[CH2:10][C:9]([OH:22])=[O:8]

Participants

4

Reactant 1

HCID 69641948HCID 69641948, compound

Product 1

HCID 22247808HCID 22247808, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

900 mg (3.03 mmol) 3-oxo-3-[[2-(2-pyridinyl)ethyl]amino]-propanoic acid phenylmethyl ester were dissolved in 25 ml THF and 15 mg palladium on charcoal (10%) were added. The reaction was kept under an atmosphere of hydrogen using a balloon for 10 hours. The mixture was filtered through dicalite. The solids were washed with THF and methanol. The combined filtrate was evaporated and dried under high vacuum. The crude product (300 mg) was used without further purification for the next reaction. 1H-NMR (CDCl3): 2.82–2.90 (m, 2H), 3.08 (s, 2H), 3.38–3.47 (m, 2H), 7.19–7.28 (m, 2H), 7.65–7.74 (m, 1H), 8.16–8.24 (m, br, 1H), 8.47–8.51 (m, H).

Workup

  1. customfor 10 hours
  2. filtrationThe mixture was filtered through dicalite
  3. washThe solids were washed with THF and methanol
  4. customThe combined filtrate was evaporated
  5. customdried under high vacuum
  6. customThe crude product (300 mg) was used without further purification for the next reaction

Sources & evidence

ORD record
ord-5e4862a0623044c0bc25af98edd25e17
Source dataset
uspto-grants-2006_02
Patent number
US06995143B2

Reaction notes

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