Ethylamine → HCID 10426278, compound

HRID 1725333Notes

Reaction equation

HRID 1725333 reaction equation
[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[C@H:10]([OH:14])[C:11]([OH:13])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].O[N:23]1[C:27]2C=CC=C[C:26]=2N=N1.Cl.C(N=C=NCCCN(C)C)C.C(N)C>CN(C=O)C.CCOC(C)=O>[CH3:4][C:1]([O:5][C:6](=[O:7])[NH:8][C@@H:9]([CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[CH:10]([OH:14])[C:11]([NH:23][CH2:27][CH3:26])=[O:13])([CH3:2])[CH3:3]

Participants

7

Reactant 4

HCID 6341EthylamineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 2762294HCID 2762294, compound

Product 1

HCID 10426278HCID 10426278, compoundYield 85.7%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

(5)(3S)-3-(tert-Butoxycarbonylamino)-2-hydroxy-4-phenylbutanoic acid (6.3 g, 21 mmol) and 1-hydroxybenzotriazole (HOBt) (3.0 g, 22.4 mmol) were dissolved in DMF (45 mL) and cooled in an ice bath. 1-Ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (EDC) (4.6 g, 24 mmol) was added, followed by aqueous ethylamine solution (3.0 mL). The solution was stirred for 18 hours. The solution was diluted into EtOAc (200 mL) and washed with 1M HCl, saturated aqueous NaHCO3, and saturated aqueous NaCl. The organic layer was dried over anhydrous MgSO4 and concentrated in vacuo to yield ((1S)-1-benzyl-3-ethylamino-2-hydroxy-3-oxo-propyl)carbamic acid 1,1-dimethylethyl ester (5.8 g, 84%) as a white solid.

Workup

  1. temperaturecooled in an ice bath
  2. washwashed with 1M HCl, saturated aqueous NaHCO3, and saturated aqueous NaCl
  3. dry with materialThe organic layer was dried over anhydrous MgSO4
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-1b3c9fba851248f89f3bb9e251481f87
Source dataset
uspto-grants-2009_02
Patent number
US07491705B2

Reaction notes

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