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Chemical Structure| 89226-13-1 Chemical Structure| 89226-13-1

Structure of 89226-13-1

Chemical Structure| 89226-13-1

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Product Details of [ 89226-13-1 ]

CAS No. :89226-13-1
Formula : C7H14N2O2S
M.W : 190.26
SMILES Code : O=C(OC(C)(C)C)NCC(N)=S
MDL No. :MFCD09025922
InChI Key :AGBIUUFZUPNDTM-UHFFFAOYSA-N
Pubchem ID :5324304

Safety of [ 89226-13-1 ]

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

Application In Synthesis of [ 89226-13-1 ]

* 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 [ 89226-13-1 ]

[ 89226-13-1 ] Synthesis Path-Downstream   1~35

  • 1
  • [ 421-20-5 ]
  • [ 89226-13-1 ]
  • [ 140903-34-0 ]
  • 3
  • [ 35150-09-5 ]
  • [ 89226-13-1 ]
YieldReaction ConditionsOperation in experiment
100% With Lawessons reagent; In tetrahydrofuran; at 20℃; for 16h; To compound 386 (21.63 g, 0.124 mol) dissolved in THF (400 mL) was added Lawesson reagent (30.13 g, 0.074 mol). Stirred at room temperature for 16 h then concentrated. Purified by silica gel chromatography (eluant: 3% MeOH- CH2CI2) then re-purified by silica gel chromatography (eluant: 2% MeOH- CH2Cl2) to give 23.59 g (100%) of the product 387 as a light green solid. MS m/e: 135 (M+2-tBu). For n=2: MS m/e: 149 (M+2-tBu)
78% With Lawessons reagent; In tetrahydrofuran; at 20℃; for 24h; Carbamoylmethyl-carbamic acid tert-butyl ester (10.88 grams, 62.46 mmol) and Lawesson's Reagent (15.66 grams, 38.72 mmol) were dissolved in THF (200 ml) and stirred under a nitrogen atmosphere at ambient temperature for 24 hours. The solvent was removed and the residue purified by column chromatography on silica (20% EtOAc/ hexanes) to yield Compound 14.2 (9.21 grams, 48.41 mmol, 78%). IH NMR (400 MHz, DMSO-d6) delta ppm 1.36 (s, 9 H) 3.80 (m, 2 H) 7.03 (m, 1 H) 8.99 (m, 1 H) 9.66 (m, 1 H).
60% With Lawessons reagent; In dichloromethane; at 20℃; for 16h;Inert atmosphere; Lawesson?s reagent (893 mg, 4.25 mmol) was added to a solution of glycineamide (740 mg, 4.25 mmol) in dry CH2Cl2 (50 mL) and the reaction mixture was stirred under N2 atmosphere at room temperature for 16 h. The reaction was quenched by addition of saturated aqueous NaHCO3 and was stirred for 1 h before been extracted with EtOAc (3 x 15 mL). The organic layers were washed with brine (20 mL); dried with MgSO4 and the solvent evaporated under reduced pressure to give the crude product wich was purified by flash chromatography (hexane/ EtOAc, 1:1) to give 8 (466 mg, 60 %) as a white solid. Rf = 0.51 (hexane/ EtOAc, 1:1); 1H NMR (400MHz, CDCl3) delta 1.46 (s, 9H), 4.16 (d, 2H, J = 6.1 Hz), 5.33 (bs, 1H), 7.66 (bs, 1H), 7.89 (bs, 1H). 13C NMR (100MHz, CDCl3) delta 28.3 (3C), 51.4, 81.1, 156.4, 205.1.
51% With Lawessons reagent; In tetrahydrofuran; at 20℃;Inert atmosphere; To a solution of N-Boc-glycinamide (2.5 g, 14.3 mmol, 1 equiv.) in anhydrous THF (20 mL) was added Lawesson's reagent (3.5 g, 8.6 mmol, 1 equiv.) under argon. The reaction mixture was stirred at rt overnight. The solvent was evaporated and the residue purified by flash chromatography using EtOAc/CH2Cl2 (1/9) to give 5 as a white solid (1.4 g, 51%)
42% With Lawessons reagent; In dichloromethane; at 20℃; for 12h; To a solution of Boc-Gly-NH2 (11 g, 62.9 mmol) in CH2Cl2 (300 mL) was added Lawesson's Reagent (13.2 g, 32.7 mmol). After stirring at rt for 12 h, the mixture was concentrated. Purification of the residue (SiO2; 50% Et2O in hexanes) provided the desired product (5.0 g, 42%).
44 g With Lawessons reagent; In tetrahydrofuran; at 20℃; for 5h; Compound 23 (42.59g, 244 . 5mmol) dissolved in tetrahydrofuran (500 ml), cooled to 0 C, plus olausson reagent (59.34g, 146 . 7mmol), stirring at room temperature to 5h, decompression turns on lathe thf, the residue is poured into the ice and saturated sodium bicarbonate solution, ethyl acetate extraction of the organic phase (500mLx3), combined with the phase, the organic phase with saturated salt water washing, dry anhydrous sodium sulfate, concentrated, the residue is dissolved in silica gel column chromatography to obtain white solid compound 24 (44g, 95%). 1 HNMR (400MHz, CDCl 3): delta 7.82 (br, 1H), 7.52 (br, 1H), 5.25 (br, 1H), 4.16 (d, J= 6.0Hz, 2H), 1.46 (s, 9H).

  • 4
  • [ 90929-73-0 ]
  • [ 89226-13-1 ]
  • [ 1001412-80-1 ]
YieldReaction ConditionsOperation in experiment
81% In acetonitrile; at 20 - 80℃; for 22h; Compound 14.1 (0.308 grams, 1.28 mmol) was mixed with Compound 14.2 (0.245 grams, 1.28 ramol) and AcCN (6 ml) was added. The reaction was stirred at ambient temperature for 20 hours followed by 80 C for 2 hours. The mixture was cooled to room temperature, diluted with EtOAc, washed with saturated sodium bicarbonate, brine, dried over sodium sulfate, filtered, and concentrated to yield Compound 14.3 (0.344 grams, 1.04 mmol, 81 %). ES (+) MS m/e = 331 (M+l).
  • 5
  • [ 1001412-89-0 ]
  • [ 89226-13-1 ]
  • [ 1001412-91-4 ]
YieldReaction ConditionsOperation in experiment
19% In ethanol; for 16h;Heating / reflux; Compound 17.1 (1.0 gram, 3.95 mmol) and Compound 14.2 (0.752 grams, 3.95 mmol) were dissolved in EtOH (20 ml) and heated at reflux for 16 hours. The mixture was cooled to ambient temperature, diluted with DCM, washed with saturated sodium bicarbonate, dried over sodium sulfate, filtered, and concentrated to yield Compound 17.2 (0.254 grams, 0.737 mmol, 19%). ES (+) MS m/e = 345 (M+l).
  • 8
  • [ 4530-20-5 ]
  • Fmoc-L-Leu-F [ No CAS ]
  • [ 89226-13-1 ]
  • 12
  • [ 89226-13-1 ]
  • {N-[3-(tert-Butoxycarbonylamino-methyl)-phenyl]-carbamimidoylmethyl}-carbamic acid tert-butyl ester; hydrobromide [ No CAS ]
  • 13
  • [ 4530-20-5 ]
  • [ 89226-13-1 ]
YieldReaction ConditionsOperation in experiment
100% With Lawessons reagent; In dichloromethane; at 25℃; for 16h; Boc-glycine (2.34 g, 0.134 mmol) was dissolved in dichloromethane (130 mL) and treated with Lawesson's reagent (2.9 g, 0.52 equivalents) and the mixture was stirred at 25 C. for 16 h. The mixture was filtered and the solvents were evaporated. The residue was purified using dichloromethane:ethyl acetate (1:1) to give 2.56 g (100%) of the thioamide.
  • 22
  • [ 89226-13-1 ]
  • [ 182120-92-9 ]
  • 26
  • [ 89226-13-1 ]
  • 2-[2-(tert-Butoxycarbonylamino-methyl)-thiazol-4-yl]-4,5-dihydro-oxazole-4-carboxylic acid methyl ester [ No CAS ]
  • 27
  • [ 89226-13-1 ]
  • [ 159379-66-5 ]
  • 28
  • [ 89226-13-1 ]
  • 2-[2-((S)-1-[2-(tert-Butoxycarbonylamino-methyl)-thiazole-4-carbonyl]-amino}-ethyl)-thiazole-4-carbonyl]-amino}-acrylic acid methyl ester [ No CAS ]
  • 29
  • [ 89226-13-1 ]
  • [ 88621-29-8 ]
  • 33
  • [ 89226-13-1 ]
  • [ 609-15-4 ]
  • ethyl 2-(tert-butoxycarbonylamino-methyl)-4-methyl-thiazole-5-carboxylate [ No CAS ]
  • 34
  • [ 4755-81-1 ]
  • [ 89226-13-1 ]
  • [ 232280-99-8 ]
YieldReaction ConditionsOperation in experiment
57.8% In methanol; at 20 - 60℃; for 50h; N-BOC-Glycine [sic] thioamide (10.0 g, 52.6 mmol) was introduced into methanol (70 ml), and methyl 2-chloroacetoacetate (7.9 g, 52.6 mmol) was added. The mixture was warmed for 2 hours at 60 C. and subsequently stirred for 48 hours at room temperature. The methanol was removed on a rotary evaporator and the residue was extracted by stirring with acetone/diethyl ether. The precipitate which remained was filtered off with suction and the filtrate was concentrated. The solid obtained from the filtrate constituted the product (pure after TLC and HPLC). Yield: 8.7 g (30.4 mmol, 57.8%). ESI-MS: 287 (M+H+)
  • 35
  • [ 363-58-6 ]
  • [ 89226-13-1 ]
  • [ 232281-06-0 ]
YieldReaction ConditionsOperation in experiment
24.5% N-BOC-Glycine [sic] thioamide (5.0 g, 26.28 mmol) was dissolved in acetonitrile (60 ml), and a solution of ethyl 2-chloro-4,4,4-trifluoroacetoacetate (6.38 g, 26.28 mmol) was added dropwise at 5-10 C. Then, the mixture was stirred for a further 30 minutes at 5 C. and for 12 hours at room temperature. The batch was then cooled to 0 C., and triethylamine (12 ml, 86.77 mmol) was added dropwise. After the mixture had been stirred for 20 minutes at 0 C., the yellow suspension had changed into a clear reddish-brown solution. Then, thionyl chloride (2.1 ml, 28.89 mmol) was slowly added dropwise at 0 C. After the mixture had been stirred for 20 minutes at 0 C., it was warmed to room temperature for a further hour. The solvent was removed on a rotary evaporator, and the residue was taken up in water (100 ml) and extracted repeatedly with ethyl acetate. The combined organic phases were dried (Na2AO4) and concentrated. The crude product was purified by chromatography (silica gel MeOH:DCM=2:98). Yield: 2.2 g (6.4 mmol, 24.5%)
 

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