Anisole → (R)-2-[(9H-Fluoren-9-ylmethoxycarbonylamino)-methyl]-butyric acid

HRID 361777Notes

Reaction equation

HRID 361777 reaction equation
[C:1]1(OC)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C([O:13][C:14](=[O:27])[CH:15]([CH2:25][CH3:26])[CH2:16][NH:17][C:18]([O:20][C:21]([CH3:24])(C)C)=[O:19])(C)(C)C>FC(F)(F)C(O)=O>[C:18]([NH:17][CH2:16][CH:15]([CH2:25][CH3:26])[C:14]([OH:13])=[O:27])([O:20][CH2:21][CH:24]1[C:2]2[C:1](=[CH:6][CH:5]=[CH:4][CH:3]=2)[C:6]2[C:1]1=[CH:2][CH:3]=[CH:4][CH:5]=2)=[O:19]

Participants

4

Reactant 2

HCID 7519AnisoleHCID 86753687N-t-butyloxycarbonyl-alpha-ethyl-beta-alanine-t-butyl ester

Product 1

HCID 64434607(R)-2-[(9H-Fluoren-9-ylmethoxycarbonylamino)-methyl]-butyric acidYield 36%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

Anisole (0.5 ml) and trifluoroacetic acid (10 ml) were added to N-t-butyloxycarbonyl-α-ethyl-β-alanine-t-butyl ester (0.98 g) and the mixture was stirred at room temperature for 12 hours. After trifluoroacetic acid was distilled off, the residue was dissolved in water (5 ml) and neutralized with a 10% aqueous solution of sodium carbonate. The product was protected with Fmoc by the same procedure as in Example 2-(3). A crystal of N-Fmoc-α-ethyl-β-alanine (437 mg, 36%) was obtained upon recrystallization from hexane.

Workup

  1. distillationAfter trifluoroacetic acid was distilled off
  2. dissolutionthe residue was dissolved in water (5 ml)

Sources & evidence

ORD record
ord-b24d176a7e234fcc94916d122a55da55
Source dataset
uspto-grants-1999_02
Patent number
US05866592

Reaction notes

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