(S)-2-[(azepane-1-carbonyl)-amino]-4-methyl-pentanoic acid benzyl ester → (2S)-2-(azepane-1-carbonylamino)-4-methylpentanoic acid

HRID 2230285Notes

Reaction equation

HRID 2230285 reaction equation
C([O:8][C:9](=[O:25])[C@@H:10]([NH:15][C:16]([N:18]1[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]1)=[O:17])[CH2:11][CH:12]([CH3:14])[CH3:13])C1C=CC=CC=1>C1COCC1.[Pd]>[N:18]1([C:16]([NH:15][C@@H:10]([CH2:11][CH:12]([CH3:14])[CH3:13])[C:9]([OH:25])=[O:8])=[O:17])[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]1

Participants

4

Reactant 1

HCID 10593708(S)-2-[(azepane-1-carbonyl)-amino]-4-methyl-pentanoic acid benzyl ester

Product 1

HCID 7530182(2S)-2-(azepane-1-carbonylamino)-4-methylpentanoic acidYield 93.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A solution of the product from Example R (2(S)-[(azepane-1-carbonyl)-amino]-4-methyl-pentanoic acid benzyl ester) (38.5 g, 111 mmol) in 600 mL of THF was hydrogenated at 50 psi over 20% Pd/C (2.00 g) for 17 minutes. The reaction mixture was filtered through celite and concentrated to dryness. The residue was heated in 50 mL of hexane. The resulting suspension was cooled and the solid collected by filtration and washed with hexane. The solid was dried at room temperature under vacuum to give the title compound as a white solid (26.6 g, 93%), mp=88-89° C.

Workup

  1. filtrationThe reaction mixture was filtered through celite and
  2. concentrationconcentrated to dryness
  3. temperatureThe residue was heated in 50 mL of hexane
  4. temperatureThe resulting suspension was cooled
  5. filtrationthe solid collected by filtration
  6. washwashed with hexane
  7. customThe solid was dried at room temperature under vacuum

Sources & evidence

ORD record
ord-cf8f6b93839f43ff8a6aaaf6adbb227b
Source dataset
uspto-grants-2002_07
Patent number
US06423689B1

Reaction notes

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