Water → Ac-DL-Lys (Ac)-OH

HRID 1106186Notes

Reaction equation

HRID 1106186 reaction equation
[NH2:1][C@H:2]([C:8]([OH:10])=[O:9])[CH2:3][CH2:4][CH2:5][CH2:6][NH2:7].N1[CH:16]=[CH:15]C=CC=1.[C:17](OC(=O)C)(=[O:19])[CH3:18].[OH2:24]>>[C:17]([NH:1][CH:2]([C:8]([OH:10])=[O:9])[CH2:3][CH2:4][CH2:5][CH2:6][NH:7][C:15](=[O:24])[CH3:16])(=[O:19])[CH3:18]

Participants

5

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 5962L-LysineHCID 7918Acetic Anhydride2×

Product 1

HCID 91827Ac-DL-Lys (Ac)-OH

Procedure

A solution of 21.9 g (0.15 mol) of L-lysine, 20 ml of pyridine, and 20 ml of water is stirred at room temperature and 40 ml (0.41 mol) of acetic anhydride is added during a 2 hour period. The resulting solution was stirred overnight at room temperature. Another 20 ml of acetic anhydride are added and the solution heated at 40° C. for 2 hours to complete the reaction and the reaction mixture is evaporated to a syrup. The crude product is purified by passing a water solution over a column of 80 g of Amberlite IR-120 resin and eluting with 1500 ml of water. The water is evaporated and the residue crystallized from acetone to afford 15.7 g of N,N'-diacetyl-DL-lysine, m.p. 138°-139° C. A second crop of 10.3 g, m.p. 138°-139° C. is obtained from acetoneacetonitrile.

Workup

  1. temperaturethe solution heated at 40° C. for 2 hours
  2. customthe reaction
  3. customthe reaction mixture is evaporated to a syrup
  4. customThe crude product is purified
  5. washeluting with 1500 ml of water
  6. customThe water is evaporated
  7. customthe residue crystallized from acetone

Sources & evidence

ORD record
ord-56e00fbe5d24436d90db8ec5e079e356
Source dataset
uspto-grants-1982_01
Patent number
US04311698

Reaction notes

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