Methanol → HCID 22794520, compound

HRID 972180Notes

Reaction equation

HRID 972180 reaction equation
O.O.[NH2:3][C@H:4]([C:10]([OH:12])=[O:11])[CH2:5][CH2:6][C:7]([OH:9])=O.[NH2:13][C@H:14]([C:20]([OH:22])=[O:21])[CH2:15][CH2:16][CH2:17][CH2:18][NH2:19].CO>CCCCCO>[NH2:3][C@H:4]([C:10]([OH:12])=[O:11])[CH2:5][CH2:6][C:7]([CH:18]([NH2:19])[CH2:17][CH2:16][CH2:15][C@@H:14]([C:20]([OH:22])=[O:21])[NH2:13])=[O:9]

Participants

4

Reactant 2

HCID 887MethanolHCID 86735116HCID 86735116, compound

Product 1

HCID 22794520HCID 22794520, compound

Reagents, catalysts & solvents 1

HCID 62761-PentanolSolvent2×

Procedure

The 350 g of the L-lysine L-glutamate dihydrate, α-phase, previously prepared, still containing approximately 15% by weight of methanol, are suspended in 0.85 liter of n-amyl alcohol in a nitrogen atmosphere. The n-amyl alcohol is then heated, followed by the distillation at around 70° first of a ternary mixture containing n-amyl alcohol, methanol and water (approximately 0.1 liter) and then of a binary mixture of n-amyl alcohol and water (approximately 0.1 liter). Heating is terminated at the reflux temperature of the n-amyl alcohol i.e. at 138° C. After a total heating time of 20 hours, the precipitate formed is separated by filtration. This gives 400 g of crude product containing ε-(γ-L-glutamyl)-L-lysine and approximately 1 liter of amylic mother liquors from which 20 g of L-pyroglutamic acid are recovered from recycling after conversion into L-glutamic acid. The n-amyl alcohol is purified for recycling.

Workup

  1. distillationfollowed by the distillation at around 70° first of a ternary mixture
  2. additioncontaining n-amyl alcohol, methanol and water (approximately 0.1 liter)
  3. additionof a binary mixture of n-amyl alcohol and water (approximately 0.1 liter)
  4. temperatureHeating
  5. customis terminated at the reflux temperature of the n-amyl alcohol i.e. at 138° C
  6. customAfter a total heating time of 20 hours, the precipitate formed
  7. customis separated by filtration
  8. additionThis gives 400 g of crude product containing ε-(γ-L-glutamyl)-L-lysine and approximately 1 liter of amylic mother liquors from which 20 g of L-pyroglutamic acid
  9. customare recovered
  10. customThe n-amyl alcohol is purified for recycling

Sources & evidence

ORD record
ord-79f68f042699453aa6942e03e37bfdbe
Source dataset
uspto-grants-1977_10
Patent number
US04052372

Reaction notes

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