N-(P-TOLUENESULFONYL)-L-PHENYLALANINE
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N-(P-TOLUENESULFONYL)-L-PHENYLALANINE
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CAS No:
13505-32-3
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Formula:
C16H17NO4S
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Chemical Name:
N-(P-TOLUENESULFONYL)-L-PHENYLALANINE
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Synonyms:
TOSYL-L-PHENYLALANINE;TOS-PHENYLALANINE-OH;TOS-PHE-OH;P-TOSYL-L-PHENYLALANINE;N-TOSYL-L-PHENYLALANINE;N-P-TOSYL-L-PHENYLALANINE;N-(P-TOLUENESULFONYL)-L-PHENYLALANINE;N-P-TOSYL-L-PHENYLALANINE97%
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CAS No:
Characteristics
91.8
2.8
1.303±0.06 g/cm3(Predicted)
165 °C
517.7±60.0 °C(Predicted)
266.9±32.9 °C
-2.8 ° (C=4.5, Acetone)
Store at RT.
1.52E-11mmHg at 25°C
N-(P-TOLUENESULFONYL)-L-PHENYLALANINE Use and Manufacturing
General procedure: Sodium carbonate (NaGeneral procedure: Sodium carbonate (Na2CO3, 1.590 g, 15 mmol) was added to a solution of amino acids (6a-h, 12.5 mmol) in water (15 mL) with continuous stirring until all the solutes dissolved. The solutionwas cooled to -5°C and an appropriate benzenesulphonyl chloride (5a-c, 15 mmol) wasadded in four portions over a period of 1 h. The slurry was further stirred at room temperaturefor 4 h. The progress of the reaction was monitored by using TLC (MeOH/DCM, 1:9). Uponcompletion, the mixture was acidified using 20percent aqueous hydrochloric acid to pH 2. The crystalswas filtered via suction and washed with pH 2.2 buffer. The pure products (7a-x) weredried over self-indicating fused silica gel in a desiccator.General procedure: Syntheses of G1 and P1: Compound 2c was synthesized from L-phenyl alanine (1.65 g, 10 mmol) viaprocedures similar to that used to synthesize 2b. Column chromatography (petroleumether: ethyl acetate = 1:1) gave 2c as a white powder: 2.40 g, 75percent, m. p. =141-143 °C. 1H NMR (400 MHz, CDCl3) δ = 7.53 (d, J = 8.2 Hz, 2H), 7.26-7.10 (m, 5H), 7.04-6.94 (m, 5H), 4.95 (d, J = 8.7 Hz, 1H), 4.15 (dt, J = 8.7, 6.0 Hz, 1H), 3.03(dd, J = 13.8, 5.4 Hz, 1H), 2.94 (dd, J = 13.9, 6.3 Hz, 1H), 2.33 (s, 1H). 13C NMR(100 MHz, CDCl3) δ =173.8, 142.8, 135.2, 133.5, 128.6, 128.3, 127.7, 126.4, 126.1, 55.2, 37.8, 20.5. NMR data were in agreement with reported results.4General procedure: The nitrogen tosylation was done using a reported procedure. In a round bottom flask, 2.4 equiv. of Na
Computed Properties
Molecular Weight:319.4
XLogP3:2.8
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:5
Rotatable Bond Count:6
Exact Mass:319.08782920
Monoisotopic Mass:319.08782920
Topological Polar Surface Area:91.8
Heavy Atom Count:22
Complexity:457
Defined Atom Stereocenter Count:1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
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