Triethylamine → (S)-N-methyl-N-methoxy-2-(tert-butoxycarbonylamino)-4-methylpentanamide

HRID 22449

Reaction equation

HRID 22449 reaction equation
C([N:3]([CH2:6]C)CC)C.[C:8]([NH:15][C@H:16]([C:21]([OH:23])=O)[CH2:17][CH:18]([CH3:20])[CH3:19])([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9].[C:24](C1NC=CN=1)(C1NC=CN=1)=[O:25]>ClCCl>[CH3:24][O:25][N:3]([CH3:6])[C:21](=[O:23])[C@H:16]([CH2:17][CH:18]([CH3:19])[CH3:20])[NH:15][C:8]([O:10][C:11]([CH3:12])([CH3:13])[CH3:14])=[O:9]

Participants

5

Reactant 3

HCID 8471Triethylamine2×HCID 83170L-Leucine, N-((1,1-dimethylethoxy)carbonyl)-HCID 5250894Bis-(1H-imidazol-2-YL)-methanone

Product 1

HCID 11119284(S)-N-methyl-N-methoxy-2-(tert-butoxycarbonylamino)-4-methylpentanamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Triethylamine (10 ml) is added to a stirred solution of Boc-Leucine in dichloromethane. Then sequentially, carbonyl-diimidazole (10 mmol) are added followed by, N-dimethylhydroxyamine hydrochloride (11 mmol), and triethylamine (11 mmol). The reaction is monitored by TLC, was found to be completely within an hour. The mixture is diluted with dicloromethane (250 ml) and washed successively with 1N HCl, and a saturated sodium chloride solution. The organic solution was dried with magnesium sulfate, and the solvent evaporated to give the desired product (9.0 mmol yield).

Workup

  1. waitto be completely within an hour
  2. washwashed successively with 1N HCl
  3. dry with materialThe organic solution was dried with magnesium sulfate
  4. customthe solvent evaporated

Sources & evidence

ORD record
ord-56486a97160b42fb8d452a058dc72998
Source dataset
uspto-grants-1995_06
Patent number
US05428019

Linked notes

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