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

HRID 1974907Notes

Reaction equation

HRID 1974907 reaction equation
[CH2:1]([O:8][C:9]([C@@H:11]([N:16]=[C:17]=[O:18])[CH2:12][CH:13]([CH3:15])[CH3:14])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH:19]1[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]1>C(OCC)(=O)C>[CH2:1]([O:8][C:9](=[O:10])[C@H:11]([CH2:12][CH:13]([CH3:14])[CH3:15])[NH:16][C:17]([N:19]1[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]1)=[O:18])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 8119AzepaneHCID 7159578HCID 7159578, compound

Product 1

HCID 10593708(S)-2-[(azepane-1-carbonyl)-amino]-4-methyl-pentanoic acid benzyl esterYield 98%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (S)-α-benzyloxycarbonyl-γ-methylbutyl isocyanate (1.50 g) in ethyl acetate (60 ml) was added hexahydro-1H-azepine (722 mg) at room temperature. After being stirred for 30 minutes at the same temperature, the solution was washed with 5% HCl, 1M sodium bicarbonate solution and saturated sodium chloride solution successively, and dried over anhydrous magnesium sulfate. The solution was concentrated in vacuo to give N-(hexahydro-1H-azepin-1-ylcarbonyl)-L-Leucine benzyl ester (2.06 g) as a crystal.

Workup

  1. washthe solution was washed with 5% HCl, 1M sodium bicarbonate solution and saturated sodium chloride solution successively
  2. dry with materialdried over anhydrous magnesium sulfate
  3. concentrationThe solution was concentrated in vacuo

Sources & evidence

ORD record
ord-6c95be62d9594f88ba2de3b318828835
Source dataset
uspto-grants-1994_02
Patent number
US05284828

Reaction notes

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