1,2-Dichloroethane → N-(t-butoxycarbonyl)-L-homophenylalaninamide

HRID 396580

Reaction equation

HRID 396580 reaction equation
[NH4+:1].[OH-:2].[C:3]([O:7][C:8]([NH:10][C@H:11](C(O)=O)[CH2:12][CH2:13][C:14]1C=CC=CC=1)=[O:9])([CH3:6])([CH3:5])[CH3:4].C(Cl)CCl.[CH:27]1[CH:28]=[CH:29][C:30]2N(O)N=N[C:31]=2[CH:32]=1>CN(C=O)C.C(Cl)Cl>[C:3]([O:7][C:8]([NH:10][C:11](=[O:2])[C@H:12]([CH2:13][CH2:14][C:31]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:32]=1)[NH2:1])=[O:9])([CH3:6])([CH3:5])[CH3:4]

Participants

7

Reactant 4

HCID 111,2-DichloroethaneHCID 14923Ammonium HydroxideHCID 757711-HydroxybenzotriazoleHCID 7018726(2S)-2-(((tert-butoxy)carbonyl)amino)-4-phenylbutanoic acid

Product 1

HCID 21339350N-(t-butoxycarbonyl)-L-homophenylalaninamideYield 78%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

NH4OH (4 mL) was added to a premixed (15 min) solution of N-(t-butoxycarbonyl)-L-homophenylalanine (4.00 g, 14.3 mmol), EDC (3.24 g, 17.2 mmol), and HOBT (2.32 g, 17.2 mmol) in DMF (20 mL) at room temperature. After 16 h the reaction mixture was diluted with CH2Cl2 and filtered, washed sequentially with 10% aqueous HCI, satd. NaHCO3, H2O (×3), brine, dried over Na2SO4, and concentrated giving N-(t-butoxycarbonyl)-L-homophenylalaninamide (3.10 g, 78%) as a white solid.

Workup

  1. filtrationfiltered
  2. washwashed sequentially with 10% aqueous HCI
  3. dry with materialNaHCO3, H2O (×3), brine, dried over Na2SO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-2af8ac02096b49868fb99442e48401a3
Source dataset
uspto-grants-2003_08
Patent number
US06608057B2

Linked notes

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