Isobutylamine → HCID 18639010, compound

HRID 1588824Notes

Reaction equation

HRID 1588824 reaction equation
[CH3:1][N:2]([C:8]([O:10][C@@H:11]([CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[C:12]([O:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[O:13])=[O:9])[CH2:3][CH2:4][C:5](O)=[O:6].[CH2:29]([NH2:33])[CH:30]([CH3:32])[CH3:31].Cl.C(N=C=NCCCN(C)C)C>C(Cl)Cl>[CH3:1][N:2]([C:8]([O:10][C@@H:11]([CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[C:12]([O:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[O:13])=[O:9])[CH2:3][CH2:4][C:5](=[O:6])[NH:33][CH2:29][CH:30]([CH3:32])[CH3:31]

Participants

5

Reactant 3

HCID 6558IsobutylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 18639008HCID 18639008, compound

Product 1

HCID 18639010HCID 18639010, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of benzyl 2(S)-[N-methyl-N-(2-carboxyethyl)aminocarbonyloxy]-3-phenylpropionate (460 mg) and isobutylamine (143 ml) in anhydrous methylene chloride (10 ml) was added N-ethyl-N'-(3-dimethylaminopropyl)carbodiimide hydrochloride (274 mg) portionwise at 0°-5° C. After being stirred at the same temperature for 3 hours, the solvent was evaporated in vacuo and the residue was dissolved in ethyl acetate (30 ml). The solution was washed with 0.5N hydrochloric acid (30 ml), water (30 ml), aqueous sodium bicarbonate (30 ml), water (30 ml) and brine (30 ml) successively, and dried over magnesium sulfate. Evaporation of the solvent gave benzyl 2(S)-[N-methyl-N-(2-isobutylcarbamoylethyl)aminocarbonyloxy]-3-phenylpropionate (440 mg) as an oil.

Workup

  1. customthe solvent was evaporated in vacuo
  2. dissolutionthe residue was dissolved in ethyl acetate (30 ml)
  3. washThe solution was washed with 0.5N hydrochloric acid (30 ml), water (30 ml), aqueous sodium bicarbonate (30 ml), water (30 ml) and brine (30 ml) successively
  4. dry with materialdried over magnesium sulfate
  5. customEvaporation of the solvent

Sources & evidence

ORD record
ord-beeefd663e3b49e494794f790be6515f
Source dataset
uspto-grants-1993_06
Patent number
US05223489

Reaction notes

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