Triethylamine → L-Alanine 1,1-dimethylethyl ester

HRID 2308893Notes

Reaction equation

HRID 2308893 reaction equation
C([N:3](CC)CC)C.FC(F)(F)S(O[C@H:14]([CH3:22])[C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])(=O)=O>ClCCl>[NH2:3][C@H:14]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH3:22]

Participants

4

Reactant 2

HCID 8471TriethylamineHCID 13563137tert-Butyl (R)-2-[(trifluoromethylsulfonyl)oxy]propionate

Product 1

HCID 89016L-Alanine 1,1-dimethylethyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 4-nitrophenylalanine, ethylester, hydrochloride (2.3 g) in dichloromethane (10 ml), add triethylamine (2.55 ml) and then t-butyl 2(R)(trifluoromethanesulfonyloxy)propionate (2.80 g) (see Preparation 4) in dichloromethane (10 ml). Stir the resulting solution at room temperature for 20 hours. Concentrate the reaction mixture, add diethyl ether and extract with salt solution. Dry over magnesium sulfate and concentrate the ether solution in vacuo to give an oil. Place the oil on a column of silica gel (100 ml, 60-200 mesh) and elute with diethyl ether:hexane 60:40 to give N-[1(S)-ethoxycarbonyl)-2-(4-nitrophenyl)ethyl]-(S)-alanine, t-butyl ester.

Workup

  1. concentrationConcentrate the reaction mixture
  2. additionadd diethyl ether
  3. extractionextract with salt solution
  4. dry with materialDry over magnesium sulfate
  5. concentrationconcentrate the ether solution in vacuo
  6. customto give an oil
  7. washelute with diethyl ether:hexane 60:40

Sources & evidence

ORD record
ord-642f42bbb9974998ae0d33e14a19e230
Source dataset
uspto-grants-1987_09
Patent number
US04691049

Reaction notes

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