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

HRID 278876Notes

Reaction equation

HRID 278876 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 (S)-2-[(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 was collected by filtration and washed with hexane. The solid was dried at room temperature under vacuum to give (S)-2-[(azepane-1-carbonyl)-amino]-4-methyl-pentanoic acid 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 was collected by filtration
  6. washwashed with hexane
  7. customThe solid was dried at room temperature under vacuum

Sources & evidence

ORD record
ord-bcbd6ef11e20417ca0c846e11fb335bc
Source dataset
uspto-grants-2002_03
Patent number
US06362174B1

Reaction notes

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