HCID 13686259, compound → N-[1(S)-ethoxycarbonyl-2-(4-nitrophenyl)ethyl]-(S)-alanine

HRID 1904877Notes

Reaction equation

HRID 1904877 reaction equation
[CH2:1]([O:3][C:4]([C@@H:6]([NH:17][C@H:18]([C:20]([O:22]C(C)(C)C)=[O:21])[CH3:19])[CH2:7][C:8]1[CH:13]=[CH:12][C:11]([N+:14]([O-:16])=[O:15])=[CH:10][CH:9]=1)=[O:5])[CH3:2]>FC(F)(F)C(O)=O>[CH2:1]([O:3][C:4]([C@@H:6]([NH:17][C@H:18]([C:20]([OH:22])=[O:21])[CH3:19])[CH2:7][C:8]1[CH:9]=[CH:10][C:11]([N+:14]([O-:16])=[O:15])=[CH:12][CH:13]=1)=[O:5])[CH3:2]

Participants

3

Reactant 1

HCID 13686259HCID 13686259, compound

Product 1

HCID 13686261N-[1(S)-ethoxycarbonyl-2-(4-nitrophenyl)ethyl]-(S)-alanine

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

Add cold trifluoroacetic acid (600 ml) (ice bath) to N-[1(S)-ethoxycarbonyl-2-(4-nitrophenyl)ethyl]-(S)-alanine, t-butyl ester (25.5 g) and stir the resulting mixture at room temperature under a nitrogen atmosphere for 4 hours. Concentrate the solution in vacuo to give a viscous oil. Triturate the viscous oil with hexane (3 l) and then ether to yield N-[1(S)-ethoxycarbonyl-2-(4-nitrophenyl)ethyl]-(S)-alanine.

Workup

  1. concentrationConcentrate the solution in vacuo
  2. customto give a viscous oil
  3. customTriturate the viscous oil with hexane (3 l)

Sources & evidence

ORD record
ord-f382c2a886634c8387dae272c58d5aeb
Source dataset
uspto-grants-1989_06
Patent number
US04840772

Reaction notes

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