ChemicalBook CAS DataBase List N-Glycyl-L-tyrosine

N-Glycyl-L-tyrosine synthesis

9synthesis methods

Product Name:N-Glycyl-L-tyrosine
CAS Number:658-79-7
Molecular formula:C11H14N2O4
Molecular Weight:238.24

1145-56-8
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$28.60/1MG

1066-33-7 Synthesis

1066-33-7
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$14.00/1Kg

658-79-7
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$11.19/1G

Yield:-

Reaction Conditions:

with ammonium hydroxide in water;

Steps:

2 EXAMPLE 2

EXAMPLE 2 Production of N-glycyl-L-tyrosine dehydrate and preparation of crystals thereof with crystal structure A 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. The obtained crude crystals (589 g, 480 g on anhydrous basis, 2.01 mol) were dissolved in 9600 ml of distilled water at 40° C. The solution was passed through a column of a weakly basic resin (WA-30 OH, 960 ml) and the fractions containing the desired compound were collected. The combined aqueous solution was concentrated under reduced pressure to 2667 ml, and 1333 ml of ethanol was added thereto, followed by recrystallization. The resulting crystals were dried under reduced pressure to give 482 g (1.76 mol, 87.5%) of the desired compound. Melting point: 277° C. (decomposition) Elemental analysis: Found: C, 48.27; H, 6.51; N, 10.21%. Calcd. for C₁₁H₁₄N₂O₄.2H₂O: C, 48.17; H, 6.61; N, 10.21%. IR absorption spectrum (KBr, cm^-1): 3361, 1668, 1537, 1458, 1421, 1389, 1240, 1148, 1115 ¹H-NMR spectrum (DMSO-d₆, δ ppm): 2.75 (dd, J=7.4, 13.6 Hz, 1H), 2.96 (dd, J=4.3, 13.6 Hz, 1H), 3.29 (d, J=16.4 Hz, 1H), 3.43 (d, J=16.4 Hz, 1H), 4.22 (m, 1H), 6.63 (d, J=7.3 Hz, 2H), 6.96 (d, J=7.7 Hz, 2H), 8.21 (m, 1H)

References:

US6197998,2001,B1