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[ CAS No. 302964-01-8 ]

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2D
Chemical Structure| 302964-01-8
Chemical Structure| 302964-01-8
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Product Details of [ 302964-01-8 ]

CAS No. :302964-01-8MDL No. :MFCD09908086
Formula : C11H16N2O4S Boiling Point : -
Linear Structure Formula :-InChI Key :-
M.W :272.32Pubchem ID :-
Synonyms :

Computed Properties of [ 302964-01-8 ]

TPSA : - H-Bond Acceptor Count : -
XLogP3 : - H-Bond Donor Count : -
SP3 : - Rotatable Bond Count : -

Safety of [ 302964-01-8 ]

Signal Word:WarningClass:
Precautionary Statements:P261-P264-P270-P271-P280-P301+P312-P302+P352-P304+P340-P305+P351+P338-P330-P332+P313-P337+P313-P362-P403+P233-P405-P501UN#:
Hazard Statements:H302-H312-H315-H319-H332-H335Packing Group:
GHS Pictogram:

Application In Synthesis of [ 302964-01-8 ]

  • Upstream synthesis route of [ 302964-01-8 ]
  • Downstream synthetic route of [ 302964-01-8 ]

[ 302964-01-8 ] Synthesis Path-Upstream   1~1

  • 1
  • [ 302964-01-8 ]
  • [ 302964-02-9 ]
YieldReaction ConditionsOperation in experiment
100%
Stage #1: With water; sodium hydroxide In methanol at 20℃;
Stage #2: With hydrogenchloride In water
To a vigorously stirred suspension of ethyl 2-(tert- butoxycarbonylamino)thiazole-5-carboxylate (4.2 g, 15 mmol) in methanol (11 mL) was added 2 M aqueous solution of NaOH (22 mL, 44.0 mmol). The suspension was stirred at room temperature overnight. The mixture was concentrated in vacuo to remove methanol. The residual aqueous suspension was acidified with 6 N aqueous solution of HCl to pH ~ 1-2. The mixture was stirred and occasionally sonicated for 1 hr. The solid was filtered, washed with water, and dried to give 2-(tert- butoxycarbonylamino)thiazole-5-carboxylic acid (3.7 g, 100percent yield) as a white solid. MS found: (M+H-Boc)+ = 145.
97.55% With ethanol; sodium hydroxide In tetrahydrofuran at 20℃; for 10 h; To 50m1 of three added in the flask THF (6m1) and ethanol (7m1), then balance for weighing Cape - 1 (1g) to join the three flasks, stir at room temperature 20min to mix uniformly; then the reaction container is transferred to the low-temperature constant in the responds the bath, the temperature dropped to 0 °C, stirring 15min; in a reaction container dropwise fresh preparation of 2 mol/L NaOH aqueous solution of 10m1, canada finishes, room temperature stirring 10h. For evaporating the reaction liquid in the Rotavapor THF; the reaction container is transferred to the low-temperature constant in the responds the bath, the temperature dropped to 0 °C, the instillment matches newly of 10percent solution of hydrochloric acid to adjust the PH to 1, separating white precipitation, filtration, the filter cake is washed with water, dried to obtain white solid product Cape - 2 (0.875g), yield 97.55percent. The total reaction equation is as follows: Nuclear magnetic with the mass spectrometry data:
89% at 25 - 30℃; for 25 h; Into a clean and dry 2 L 4-neck round bottom flask connected to a mechanical stirrer, condenser, thermometer socket is charged with 600 mL of 6N NaOH solution and slowly add 25 g of ethyl 2-tert-butoxycarbonylaminothiazole-5-carboxylate (2) to the 6N NaOH solution at 25-30 °C within 30-60 min period. Maintained the reaction mass at 25-30 °Cfor 24 h and after TLC compliance added 6N HCl solution (600 mL) to the reaction mass at 25-30 °C within 60-90 min period (pH test limit should be 0.5-1.5). Maintained the reaction mass at 25-30 °C for 60-90 min period and transferred the reaction mass into a Buchner funnel and flask kept under plant vacuum. Washed the wet cake with 100 mL DM water and dried the above wet material in the dryer at 60-65°C for 6-8 h to furnish 17 g of the title compound with purity above 99 percent. Off white colour solid; Elemental analysis C9H12N2O4Scalcd (found) percent: C 44.25 (44.55), H 4.95 (4.72), N 11.47 (11.31),O 26.20 (26.07), S 13.13 (13.16). IR (KBr, νmax, cm-1): 3434.68,3167.64, 2980.51, 1727.41, 1672.79, 1576.45, 1522.35; 1H NMR (400 MHz, DMSO-d6): δ1.506 (s, 9H, -3CH3), 7.970 (s,1H, ArH), 11.937 (s, 2H, -NH & -OH); 13C NMR (100 MHz,DMSO-d6): δ164.34, 163.09, 152.91, 145.39, 122.46, 82.40,28.04; ESI-MS (m/z): 245.12 (M+1), 246.13 (M+2)
86%
Stage #1: at 20℃; for 12 h;
Stage #2: With hydrogenchloride; water In ethanol
A solution of ethyl 2-(tert-butoxycarbonylamino)thiazole-5-carboxylate (5 g, 18.36 mmol) and KOH (10.3 g, 184 mmol) in EtOH/H2O (1 :1) (60 mL) was stirred at RT for 12 hrs. The solution was acidified with IN HCl and the precipitate was filtered and dried, yielding 2-(tert- butoxycarbonylamino)thiazole-5-carboxylic acid (3.84 g, 86percent) as a white solid. 1H-NMR (400 MHz, DMSOd6): δ(ppm): 12.0 (bs, IH), 7.94 (s, IH), 1.5 (s, 9H). 10. MS (ESI): m/z (percent): 245.35 [MH+].
17.0 g at 25 - 30℃; Into a clean and dry 2.0.L 4-neck RB flask charged 600 ml of 6N-NaOH (0069) solution. Slowly added ethyl 2-tert-butoxy-carbonylamino-thiazole-5- carboxylate (20gm) to the 6N-NaOH solution at temperature 25-30°C within 30- 60 min period.Maintained the reaction mass temperature at 25-30°C for 24hrs. after completion of the reaction, added 6N-HC1 solution to the reaction mass at temperature 25-30°C within 60-90 min period, maitained the reaction mass at temperature 25-30°C for 60-90 min period, transfered the reaction mass into a buchner funnel and flask kept under lant vacuum. Wash the wet cake with (0070) 100.0ml DM Water, suck dried thoroughly for 30-45 min. Transfered the wet material into a clean and dry petridish. Dried the above wet material in drier at temperature 60-65 C for 6-8 hrs. (0071) Weight: 17.0

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