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Chemical Structure| 1738-76-7 Chemical Structure| 1738-76-7
Chemical Structure| 1738-76-7

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Product Details of H-Gly-OBzl.TosOH

CAS No. :1738-76-7
Formula : C16H19NO5S
M.W : 337.39
SMILES Code : O=C(OCC1=CC=CC=C1)CN.CC2=CC=C(S(=O)(O)=O)C=C2
MDL No. :MFCD00035425
InChI Key :WJKJXKRHMUXQSL-UHFFFAOYSA-N
Pubchem ID :6451311

Safety of H-Gly-OBzl.TosOH

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Application In Synthesis of H-Gly-OBzl.TosOH

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 1738-76-7 ]

[ 1738-76-7 ] Synthesis Path-Downstream   1~6

  • 2
  • [ 59969-65-2 ]
  • [ 1738-76-7 ]
  • [ 62023-09-0 ]
  • 3
  • [ 1738-76-7 ]
  • [ 49827-15-8 ]
  • [ 171557-57-6 ]
  • 4
  • [ 364750-81-2 ]
  • [ 1738-76-7 ]
  • [ 901139-29-5 ]
YieldReaction ConditionsOperation in experiment
84% With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; In dichloromethane; for 27h; Compound 9 (1.6 g, 7.0 mmol), glycine benzyl ester tosylate (3.07 g, 9.1 mmol), and PyBOP (3.64 g, 7.0 mmol) were dissolved in anhydrous CH2Cl2 (80 mL). DIEA (2.26 g, 17.5 mmol) was added, and the resulting solution was stirred for 27 h under Ar(g). The reaction mixture was washed with 10percent w/v aqueous citric acid (3.x.50 mL), NaHCO3 (3.x.50 mL), water (50 mL), and brine (50 mL), dried over anhydrous MgSO4(s), and concentrated under reduced pressure. The crude oil was purified by flash chromatography (1:1 EtOAc:hexane) to afford 11 (2.13 g, 5.9 mmol, 84percent) as a colorless, sticky liquid. 1H NMR delta: 1.03 and 1.04 (d, J=3.2, 3H), 1.44 (bs, 9H), 1.55-2.50 (m, 4H), 2.90 (t, J=9.8, 1H), 3.65-3.94 (m, 1H), 4.01-4.34 (m, 3H), 5.18 (s, 2H), 7.36 (bs, 5H); HRMS-ESI (m/z): [M+Na]+ calcd for C20H28N2O5Na, 399.1896; found, 399.1897.
  • 5
  • [ 1738-76-7 ]
  • [ 71239-85-5 ]
  • [ 337530-28-6 ]
YieldReaction ConditionsOperation in experiment
With diphenyl phosphoryl azide; N-ethyl-N,N-diisopropylamine; In DMF (N,N-dimethyl-formamide); at 4 - 20℃; for 3.0h; To a solution of (2S)-2-[(tert-butoxycarbonyl)amino]-3-(2-pyridyl)propanoic acid (55.0 g), glycine benzyl ester tosylate (69.7 g), and diphenylphosphoryl azide (46.7 ml) in N,N-dimethylformamide (550 ml) was added dropwise N,N-diisopropylethylamine (75.6 ml) at 4 C. The mixture was warmed to room temperature and stirred for 3 hours. The resulting mixture was poured into ice-cold saturated aqueous sodium hydrogencarbonate solution (700 ml). The mixture was extracted twice with ethyl acetate (total 1.3 L) and washed successively with water (400 ml×2), saturated aqueous ammonium chloride solution (200 ml), aqueous sodium hydrogencarbonate solution (300 ml×2), and brine (40 ml). The organic layer was dried over anhydrous magnesium sulfate and concentrated to give the title compound (77.4 g) as pale brown crystals. [00175] ESI-MS: 414.3(H+H) [00176] 1H-NMR (300 MHz, CDCl3) delta 8.48 (dd, J=5 Hz,2 Hz, 1H), 7.82 (br, 1H), 7.60 (td, J=8 Hz,2 Hz, 1H), 7.40-7.29 (m, 5H), 7.21 (d, J=8 Hz, 1H), 7.14 (dd, J=8 Hz,5 Hz, 1H), 6.33 (br, 1H), 5.15 (s, 2H), 4.62 (br, 1H), 4.04 (d, J=6 Hz, 2H), 3.36-3.18 (m, 2H), 1.43 (s, 9H).
  • 6
  • [ 34404-33-6 ]
  • [ 1738-76-7 ]
  • [ 64410-44-2 ]
YieldReaction ConditionsOperation in experiment
With 4-methyl-morpholine; In N,N-dimethyl-formamide; at 25℃;pH 7.2 - 7.5; Dissolve 907 g of H-Gly(OBzl)*Tos in 3 L of DMF, adjust pH to 7.2-7.5 with N-methylmorpholine. Add a solution of 773 g of <strong>[34404-33-6]Boc-Ala-ONSu</strong> in 2 L DMF in a single portion under cooling on a water bath. T<25 C. Remove the bath and stir at room temperature. TLC control. Evaporate DMF on a rotary evaporator at 41 C. under the vacuum of a rotary vane pump. Dissolve the resulting oil in 15 L of ethyl acetate and transfer to a glass desiccator equipped with a stirrer. Wash the organic layer 3 times with 3 L portions of water. Bring 200 mL of saturated Na2CO3 solution to 3 L with water, wash the organic layer with this solution, then wash 3 more times with 3 L portions of water. Prepare a solution of 6.5 mL 20% sulfuric acid in 3 L of water, wash the organic layer with this solution, then wash 3 more times with 3 L portions of water. At each washing add 0.5 L of ethyl acetate. Evaporate ethyl acetate on a rotary evaporator at 41 C. under the vacuum of a diaphragm pump.
 

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