Ammonium Bicarbonate → Glycyl-L-tyrosine

HRID 1531470Notes

Reaction equation

HRID 1531470 reaction equation
C(=O)([O-])O.[NH4+:5].Cl[CH2:7][C:8]([NH:10][C@H:11]([C:20]([OH:22])=[O:21])[CH2:12][C:13]1[CH:18]=[CH:17][C:16]([OH:19])=[CH:15][CH:14]=1)=[O:9]>N.O>[NH2:5][CH2:7][C:8]([NH:10][C@H:11]([C:20]([OH:22])=[O:21])[CH2:12][C:13]1[CH:18]=[CH:17][C:16]([OH:19])=[CH:15][CH:14]=1)=[O:9]

Participants

5

Reactant 2

HCID 14013Ammonium BicarbonateHCID 2724332N-(2-Chloroacetyl)-L-tyrosine

Product 1

HCID 92829Glycyl-L-tyrosine

Reagents, catalysts & solvents 2

HCID 222AmmoniaSolventHCID 962WaterSolvent2×

Conditions

Temperature
40 °C

Procedure

Ammonium hydrogencarbonate (1289 g) was dissolved in a mixture of 4000 ml of 28% aqueous ammonia and 1000 ml of distilled water at 35° C. To the solution were added 700 g (2.72 mol) of N-chloroacetyl-L-tyrosine and 700 ml of distilled water, followed by stirring at 40° C. for 5 hours. The reaction mixture was concentrated under reduced pressure to remove excess ammonia and then adjusted to pH 5.5 with concentrated hydrochloric acid at 45° C., followed by gradual cooling. After crystals were deposited, the mixture was ice-cooled and the crystals were isolated by filtration to give 600 g (489 g on anhydrous basis, 2.05 mol, 75.4%) of crude crystals of N-glycyl-L-tyrosine.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customto remove excess ammonia
  3. customadjusted to pH 5.5 with concentrated hydrochloric acid at 45° C.
  4. temperaturecooled
  5. customthe crystals were isolated by filtration

Sources & evidence

ORD record
ord-30c8d1b2f7a44c748de54590ed461828
Source dataset
uspto-grants-2001_03
Patent number
US06197998B1

Reaction notes

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