Trifluoroacetic acid → L-alanine, 2-(benzyloxycarbonylamino)ethyl amide

HRID 1779911Notes

Reaction equation

HRID 1779911 reaction equation
[CH2:1]([O:8][C:9]([NH:11][CH2:12][CH2:13][NH:14][C:15](=[O:26])[C@H:16]([CH3:25])[NH:17]C(OC(C)(C)C)=O)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.FC(F)(F)C(O)=O>ClCCl>[CH2:1]([O:8][C:9]([NH:11][CH2:12][CH2:13][NH:14][C:15](=[O:26])[C@H:16]([CH3:25])[NH2:17])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 54526617HCID 54526617, compound

Product 1

HCID 57139072L-alanine, 2-(benzyloxycarbonylamino)ethyl amideYield 90%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 12.0 g (0.033 mol) of (1g) in 25 ml of dichloromethane was cooled with an ice bath and 25 ml of trifluoroacetic acid was added. The solution was stirred at ca 5° C. for 20 minutes, then allowed to stir to room temperature. After 90 minutes, the dichloromethane and trifluoroacetic acid were removed in vacuo. The resulting residue was dissolved in 200 ml of ethyl acetate and washed with 2M sodium hydroxide (200 ml) and brine (100 ml). After drying over anhydrous magnesium sulfate, the solution was filtered and concentrated in vacuo to produce 7.86 g (90% yield) of L-alanine, 2-(benzyloxycarbonylamino)ethyl amide (1h) as a white solid. 1H NMR(CDCl3) δ 1.28(d, 3H), 2.09(m, 2H), 3.33(m, 4H), 3.47(q, 1H), 5.07(s, 2H), 5.59(bt, 1H), 7.33(bs, 5H), 7.69(bt, 1H);13C NMR (CDCl3) δ 21.3, 39.5, 40.9, 50.4, 66.6, 128.0, 128.1, 128.4, 136.4, 156.9, 176.7.

Workup

  1. stirringto stir to room temperature
  2. waitAfter 90 minutes
  3. customthe dichloromethane and trifluoroacetic acid were removed in vacuo
  4. dissolutionThe resulting residue was dissolved in 200 ml of ethyl acetate
  5. washwashed with 2M sodium hydroxide (200 ml) and brine (100 ml)
  6. dry with materialAfter drying over anhydrous magnesium sulfate
  7. filtrationthe solution was filtered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-3bb3ef5e0af843dab6f398ce3a34f80e
Source dataset
uspto-grants-1997_05
Patent number
US05629285

Reaction notes

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