L-Alanine ethyl ester → HCID 10085120, compound

HRID 1755979Notes

Reaction equation

HRID 1755979 reaction equation
[C:1](=[NH:14])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:15]([O:17][C:18](=[O:22])[C@H:19]([CH3:21])N)[CH3:16]>C(Cl)Cl>[C:2]1([C:1]([C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)=[N:14][C@H:19]([C:18]([O:17][CH2:15][CH3:16])=[O:22])[CH3:21])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 76507L-Alanine ethyl esterHCID 136809Benzophenone imine

Product 1

HCID 10085120HCID 10085120, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Benzophenone imine (53.4 g, 286 mmol) was dissolved in methylene chloride (400 mL) and stirred at room temperature. To the solution was added L-alanine ethyl ester (43.9 g, 286 mmol) and the reaction stirred at room temperature for 48 hours. The reaction was washed 3 times with water (200 mL). The organic layer was separated, dried (MgSO4), and the filtrate was concentrated in vacuo to give a clear oil. The oil was crystallized from pentane to give the title compound (72.1 g, 90%), FAB-MS 282 (MH+).

Workup

  1. stirringthe reaction stirred at room temperature for 48 hours
  2. washThe reaction was washed 3 times with water (200 mL)
  3. customThe organic layer was separated
  4. dry with materialdried (MgSO4)
  5. concentrationthe filtrate was concentrated in vacuo
  6. customto give a clear oil
  7. customThe oil was crystallized from pentane

Sources & evidence

ORD record
ord-ee9d2b691b6b40928703085cb0e8ab80
Source dataset
uspto-grants-1995_08
Patent number
US05439888

Reaction notes

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