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[ CAS No. 59511-72-7 ] {[proInfo.proName]}

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Chemical Structure| 59511-72-7
Chemical Structure| 59511-72-7
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Product Details of [ 59511-72-7 ]

CAS No. :59511-72-7 MDL No. :
Formula : C11H12N2O3 Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W : 220.23 Pubchem ID :-
Synonyms :

Safety of [ 59511-72-7 ]

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Application In Synthesis of [ 59511-72-7 ]

* 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 [ 59511-72-7 ]

[ 59511-72-7 ] Synthesis Path-Downstream   1~14

  • 1
  • [ 288-32-4 ]
  • [ 1189-71-5 ]
  • HP20AG resin [ No CAS ]
  • [ 29420-49-3 ]
  • [ 59511-72-7 ]
  • [ 741629-02-7 ]
YieldReaction ConditionsOperation in experiment
With tetra(n-butyl)ammonium hydrogen sulfate; triethylamine; In (2S)-N-methyl-1-phenylpropan-2-amine hydrate; dichloromethane; water; acetone; EXAMPLE 31 (S)-N-(1-Imidazolylsulfonyl)-2-oxo-3-[[(phenylmethoxy) carbonyl]amino]- 1-azetidinecarboxamide, potassium salt (S)-(2-Oxo-3-azetidinyl)carbamic acid, phenylmethyl ester (3 g) was suspended in 100 ml of dry dichloromethane and cooled to -5 C. Chlorosulfonyl isocyanate (2.1 g) in 10 ml of dichloromethane was dropped in with stirring, which was continued for 45 minutes. Triethylamine (3.5 g) and 1.02 g of imidazole were added and the solution was stirred overnight at 0 C. After the addition of 4.6 g of tetrabutylammonium hydrogen sulfate in 200 ml of ice water, the pH is adjusted to 6.5 with 1N potassium hydroxide. The organic layer was separated, dried (sodium sulfate), filtered and evaporated to dryness. The residue was treated with 4.6 g of potassium perfluorobutanesulfonate in 50 ml of acetone. This solution was poured into 200 ml of ether and crude product (4.5 g) was filtered off. Purification was accomplished by chromatography using HP20AG resin and water/acetone (8:2) as eluant, yielding 1.7 g of the title compound melting point 130 C., dec.
  • 2
  • [ 1189-71-5 ]
  • N-(2,5-dioxo-1-imidazolidinyl)-1,4-dihydro-4-oxo-5-hydroxy-2-pyridinecarboxamide [ No CAS ]
  • [ 24589-78-4 ]
  • [ 59511-72-7 ]
  • phenylmethyl ester [ No CAS ]
  • (S)-[1-[[[[3-[[(1,4-dihydro-5-hydroxy-4-oxo-2-pyridinyl)carbonyl]amino]-2,4-dioxo-1-imidazolidinyl]sulfonyl]amino]carbonyl]-2-oxo-3-azetidinyl]carbamic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
With sodium hydrogencarbonate In water; ethyl acetate; acetone 1.C (C) To a suspension of 6.1 g (0.0242 mol) of N-(2,5-dioxo-1-imidazolidinyl)-1,4-dihydro-4-oxo-5-hydroxy-2-pyridinecarboxamide in 200 ml of ethyl acetate was added 19.48 ml of N-methyl-N-(trimethylsilyl)trifluoroacetamide (0.105 mol) at room temperature. The mixture was stirred at room temperature for 1 hour. After stirring for 10 minutes, a clear solution was formed (solution A). To a suspension of 5.32 g of (S)-(2-oxo-3-azetidinyl)carbamic acid, phenylmethyl ester (0.242 mol) in 200 ml of ethyl acetate was added at room temperature with stirring 2.11 ml (0.0242 mol) of chlorosulfonylisocyanate. The mixture was stirred at room temperature for 1 hour. After 10 minutes, a clear solution was formed (solution B). Solution A was added, with cooling, to solution B and the mixture was stirred overnight at room temperature. Then the solution was evaporated in vacuo and the remaining syrup dissolved in a mixture of 150 ml of acetone and 150 ml of water. The pH of the clear solution was adjusted to 5-5.5 by the addition of a sodium bicarbonate solution. The solution as kept at this pH for 2 hours. Then the acetone was removed in vacuo, and the aqueous solution lyophilized to yield 14.6 g of crude of (S)-[1-[[[[3-[[(1,4-dihydro-5-hydroxy-4-oxo-2-pyridinyl)carbonyl]amino]-2,4-dioxo-1-imidazolidinyl]sulfonyl]amino]carbonyl]-2-oxo-3-azetidinyl]carbamic acid, phenylmethyl ester, sodium salt. The crude material was purified by chromatography on XAD by elution with water/acetone (9:1). Yield: 2.5 g of purified product.
  • 3
  • [ 1189-71-5 ]
  • (S)-[1-[[[[2-[(3,4-dihyroxyphenyl)[[(t-butyloxy)carbonyl]amino]acetyl]hydrazino]sulfonyl]amino]carbonyl]-2-oxo-3-azetidinyl]carbamic acid, phenylmethyl ester [ No CAS ]
  • (S)-[1-[[[[2-[(3,4-dihydroxyphenyl)[[(t-butyloxy)carbonyl]amino]acetyl]hydrazino]sulfonyl]amino]carbonyl]-2-oxo-3-azetidinyl]carbamic acid, phenylmethyl ester [ No CAS ]
  • 3,4-dihydroxy-α-[[(phenylmethoxy)carbonyl]amino]benzoic acid [ No CAS ]
  • [ 24589-78-4 ]
  • [ 59511-72-7 ]
  • (S)-[1-[[[[2-[(3,4-dihydroxyphenyl)[[(phenylmethoxy)carbonyl]amino]acetyl]hydrazino]sulfonyl]amino]carbonyl]-2-oxo-3-azetidinyl]carbamic acid, phenylmethyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
With hydrogenchloride; sodium hydroxide; triethylamine In methanol; dichloromethane; water; ethyl acetate; Petroleum ether 14.A (A) (A) (S)-[1-[[[[2-[(3,4-dihydroxyphenyl)[[(phenylmethoxy)carbonyl]amino]acetyl]hydrazino]sulfonyl]amino]carbonyl]-2-oxo-3-azetidinyl]carbamic acid, phenylmethyl ester 3.91 ml (0.020 mol) of N-Methyl-N-trimethylsilyltrifluoroacetamide was added to a suspension of 2.97 g (0.010 mol) of 3,4-dihydroxy-α-[[(phenylmethoxy)carbonyl]amino]benzoic acid, hydrazide of dry ethyl acetate. After stirring for 3 hours at 50° C., the clear solution was evaporated in vacuo and the residue was dissolved in 20 ml of dry ethyl acetate (solution A). To a suspension of 2.20 g (0.010 mol) of (S)-(2-oxo-3-azetidinyl)carbamic acid, phenylmethyl ester in 80 ml of dry ethyl acetate, 0.90 ml (0.010 mol) of chlorosulfonylisocyanate was added with stirring and the mixture was stirred for 1 hour at room temperature and then cooled to 0° C. After the addition of 20 ml of dry dichloromethane and 4.18 ml (0.030 mol) of triethylamine, solution A was dropped in with stirring at 0° C. Stirring was continued for 10 minutes at 0° C. and 2.5 hours at room temperature. Then the reaction mixture was poured into 150 ml of an ice cold buffer solution (citrate pH 3). The pH was maintained by the addition of 2N hydrochloric acid (pH=3). The organic layer was separated and the aqueous phase was extracted with ethyl acetate. The organic layers were combined, washed with brine, dried (magnesium sulfate) and evaporated in vacuo to leave a solid foam. This crude mixture of diastereomers of (S)-[1-[[[[2-[(3,4-dihydroxyphenyl)[[(t-butyloxy)carbonyl]amino]acetyl]hydrazino]sulfonyl]amino]carbonyl]-2-oxo-3-azetidinyl]carbamic acid, phenylmethyl ester was stirred with petroleum ether containing a few ml of ether until it became crystalline; yield: 7.1 g. The crystalline mixture of diastereomers of (S)-[1-[[[[2-[(3,4-dihyroxyphenyl)[[(t-butyloxy)carbonyl]amino]acetyl]hydrazino]sulfonyl]amino]carbonyl]-2-oxo-3-azetidinyl]carbamic acid, phenylmethyl ester was dissolved in 35 ml of methanol. After the addition of 17 ml of water, the pH of the solution was adjusted to 6.0 by the addition of dilute (1%) sodium hydroxide solution. The solution was concentrated in vacuo until an oil was separated which solidified by stirring with ether; yield: 3.3 g. Freeze drying of the aqueous phase yielded, after stirring with ether, an additional 2.5 g of (S)-[1-[[[[2-[(3,4-dihydroxyphenyl)[[(t-butyloxy)carbonyl]amino]acetyl]hydrazino]sulfonyl]amino]carbonyl]-2-oxo-3-azetidinyl]carbamic acid, phenylmethyl ester.
  • 4
  • [ 1189-71-5 ]
  • N-(3,4-Dihydroxyphenylcarbonylamino)piperazindione [ No CAS ]
  • [ 24589-78-4 ]
  • [ 59511-72-7 ]
  • (S)-[1-[[[[4-[(3,4-dihydroxybenzoyl)amino]-2,3-dioxo-1-piperazinyl]sulfonyl]amino]carbonyl]-2-oxo-3-azetidinyl]carbamic acid, phenylmethyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
With hydrogenchloride; triethylamine In dichloromethane; ethyl acetate 9.C (C) (C) (S)-[1-[[[[4-[(3,4-Dihydroxybenzoyl)amino]-2,3-dioxo-1-piperazinyl]sulfonyl]amino]carbonyl]-2-oxo-3-azetidinyl]carbamic acid, phenylmethyl ester To a suspension of 1.90 g (7.16 mmol) of N-(2,3-dioxo-1-piperazinyl)-3,4-dihydroxybenzamide in 30 ml of absolute ethyl acetate was added 5.70 g (28.64 mmol) of N-methyl-N-(trimethylsilyl)trifluoroacetamide, and the mixture was stirred for 3 hours at 60° C. The clear solution was evaporated to dryness and the crystalline residue suspended in 30 ml of ethyl acetate (solution A). To a suspension of 1.58 g (7.16 mmol) of (S)-(2-oxo-3-azetidinyl)carbamic acid, phenylmethyl ester in 50 ml of ethyl acetate was added 1.01 g (7.16 mmol) of chlorosulfonyl isocyanate. After stirring for 1 hour at room temperature, the solution was cooled to 0° C. and 24 ml of dichloromethane and 2.17 g (21.48 mmol) of triethylamine were added (solution B). To solution B, solution A was added dropwise at 0° C. After stirring overnight, ice was added and the pH brought to 1 with 3N hydrochloric acid. After stirring for 3 hours, the phases were separated. The organic phase was washed with water and the aqueous phase back-extracted two times with ethyl acetate. The combined organic phases were dried and evaporated to afford 3.0 g of crude material which was triturated with ether to yield 2.94 g of (S)-[1-[[[[4-[(3,4-dihydroxybenzoyl)amino]-2,3-dioxo-1-piperazinyl]sulfonyl]amino]carbonyl]-2-oxo-3-azetidinyl]carbamic acid, phenylmethyl ester.
  • 5
  • [ 1189-71-5 ]
  • 2-amino-N-(3,4-dihydroxyphenyl)acetamide [ No CAS ]
  • [ 24589-78-4 ]
  • [ 59511-72-7 ]
  • (S)-[1-[ [[[[2-[(3,4-Dihydroxyphenyl]amino]-2-oxoethyl]amino]sulfonyl]amino]carbonyl]-2-oxo-3-azetidinyl]carbamic acid, phenylmethyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
With triethylamine In (2S)-N-methyl-1-phenylpropan-2-amine hydrate; dichloromethane; ethyl acetate; acetonitrile 17.C (C) (C) (S)-[1-[ [[[[2-[(3,4-Dihydroxyphenyl]amino]-2-oxoethyl]amino]sulfonyl]amino]carbonyl]-2-oxo-3-azetidinyl]carbamic acid, phenylmethyl ester To a suspension of 1.24 g (6.79 mmol) of 2-amino-N-(3,4-dihydroxyphenyl)acetamide in 30 ml of absolute acetonitrile was added 2.71 g (13.6 mmol) of N-methyl-N-(trimethylsilyl)trifluoroacetamide. After stirring for two hours, the clear solution was evaporated to dryness, finally at high vacuum at 55° C. The residue was dissolved in 30 ml of ethyl acetate (solution A). To a suspension of 1.5 g (6.79 mmol) of (S)-(2-oxo-3-azetidinyl)carbamic acid, phenylmethyl ester in 40 ml of ethyl acetate was added 0.96 g (6.79 mmol) of chlorosulfonyl isocyanate. After stirring for one hour, the solution was cooled to 0° C. and 15 ml of dichloromethane and subsequently 2.06 g (20.37 mmol) of triethylamine (dropwise) was added. To this mixture, solution A was added dropwise and after stirring overnight at room temperature, 30 ml of ice water was added. The pH was adjusted to 1 with 3N hydrochloric acid, the phases were separated and the organic phase was dried over sodium sulfate. After the evaporation of the solvent, the residue was triturated with ether, filtered and dried in vacuo; yield: 1.63 g.
  • 6
  • 3-[[(1,4-dihydro-5-hydroxy-4-oxo-2-pyridinyl)-carbonyl]-amino]tetrahydro-2-oxo-1(2H)-pyrimidinecarboxamide [ No CAS ]
  • [ 24589-78-4 ]
  • [ 59511-72-7 ]
  • (S)-[1-[[[[[[3-[[(1,4-Dihydro-5-hydroxy-4-oxo-2-pyridinyl)-carbonyl]amino]tetrahydro-2-oxo-1(2H)-pyrimidinyl]carbonyl]amino]-sulfonyl]amino]carbonyl]-2-oxo-3-azetidinyl]carbamic acid, phenylmethyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
In ethyl acetate chlorosulfonyl isocyanate; dichloromethane; water; ethyl acetate; acetonitrile 2.F (F) (F) (S)-[1-[[[[[[3-[[(1,4-Dihydro-5-hydroxy-4-oxo-2-pyridinyl)-carbonyl]amino]tetrahydro-2-oxo-1(2H)-pyrimidinyl]carbonyl]amino]-sulfonyl]amino]carbonyl]-2-oxo-3-azetidinyl]carbamic acid, phenylmethyl ester To a suspension of (S)-(2-oxo-3-azetidinyl)carbamic acid, phenylmethyl ester (6.61 g, 30.0 mmol) in 300 ml ethyl acetate chlorosulfonyl isocyanate (4.25 g, 30.0 mmol) was added, and the mixture was stirred for 1 hour at room temperature (solution A). To a solution of 3-[[(1,4-dihydro-5-hydroxy-4-oxo-2-pyridinyl)-carbonyl]-amino]tetrahydro-2-oxo-1(2H)-pyrimidinecarboxamide (8.86 g, 30.0 mmol) in 300 ml ethyl acetate, N-methyl-N-trimethylsilyltrifluoroacetamide (23.91 g, 120 mmol) was added. After 30 minutes a clear solution was obtained; 300 ml dichloromethane was added, followed by the dropwise addition of solution A at 0° C. After stirring overnight at room temperature 300 ml water was added whereupon an oily residue separated. The solvents were decanted off and the residue triturated with ether to give 10.27 g of the desired product (crude). The product was suspended in water and the pH adjusted to 6 with 2N sodium hydroxide. After freeze drying of the resulting solution the product was chromatographed in four portions on XAD under mplc conditions with water and water:acetonitrile 9:1 as eluents. The product-containing fractions were freeze dried to give a total of 5.2 g of the desired product.
  • 7
  • [ 1189-71-5 ]
  • [ 24589-78-4 ]
  • [ 26961-27-3 ]
  • [ 59511-72-7 ]
  • [ 114903-84-3 ]
YieldReaction ConditionsOperation in experiment
With triethylamine In dichloromethane; ethyl acetate; Petroleum ether 16.B (B) (B) (S)-[1-[[[[(2-cyano-4,5-dihydroxyphenyl)amino]sulfonyl]amino]carbonyl]-2-oxo-3-azetidinyl]carbamic acid, phenylmethyl ester To a suspension of 4.5 g (30.0 mmol) of 2-amino-4,5-dimethoxybenzonitrile in 60 ml of absolute ethyl acetate was added 12.0 g (60.0 mmol) of N-methyl-N-(trimethylsilyl)trifluoroacetamide. After stirring for 1.5 hours, the clear solution was evaporated to dryness, finally at high vacuum at 50° C. The residue was dissolved in 55 ml of ethyl acetate (solution A). To a suspension of 6.6 g (30.0 mmol) of (S)-(2-oxo-3-azetidinyl)carbamic acid, phenylmethyl ester in 150 ml of ethyl acetate was added 4.65 g (33.0 mmol) of chlorosulfonyl isocyanate. After stirring for 1 hour, the solution was cooled to 0° C. and 50 ml of dichloromethane and 9.0 g (90.0 mmol) of triethylamine (dropwise) were added. To this mixture, solution A was added dropwise at 0° C. and after stirring overnight at room temperature, the mixture was poured into ice water. The pH was adjusted to 2.0 with 3N hydrochloric acid. The organic phase was separated and the aqueous phase extracted twice with ethyl acetate. The combined organic phases were extracted twice with brine and dried over sodium sulfate. Evaporation of the solvent yielded 13.5 g of crude product which was slurried twice, each time with 200 ml of ether for 2 hours; yield of crystalline material after drying: 6.5 g. When petroleum ether was added to the ether layers, another 3.5 g of pure product was precipitated. Total yield: 10.0 g; melting point 111.9° C., dec.
  • 8
  • [ 1189-71-5 ]
  • 1-[[[3,4-bis[(trimethylsilyl)oxy]phenyl]methylene]amino]-3-(trimethylsilyl)-2-imiazolidinone [ No CAS ]
  • [ 24589-78-4 ]
  • [ 59511-72-7 ]
  • (S)-[1-[[[[3-[[(3,4-dihydroxyphenyl)methylene]amino]-2-oxo-1-imidazolidinyl]sulfonyl]amino]carbonyl]-2-oxo-3-azetidinyl]carbamic acid, phenylmethyl ester, monosodium salt [ No CAS ]
YieldReaction ConditionsOperation in experiment
With sodium hydroxide In methanol; water; ethyl acetate 7.C (C) (C) (S)-[1-[[[[3-[[(3,4-Dihydroxyphenyl)methylene]amino]-2-oxo-1-imidazolidinyl]sulfonyl]amino]carbonyl]-2-oxo-3-azetidinyl]carbamic acid, phenylmethyl ester, monosodium salt To a suspension of 4.37 g (19.9 mmol) of (S)-(2-oxo-3-azetidinyl)carbamic acid, phenylmethyl ester in 100 ml of ethyl acetate were added 2.81 g (19.9 mmol) of chlorosulfonyl isocyanate and the mixture was stirred for one hour at room temperature. The resulting solution was cooled to 0° C., and a solution of 8.7 g (19.9 mmol) of 1-[[[3,4-bis[(trimethylsilyl)oxy]phenyl]methylene]amino]-3-(trimethylsilyl)-2-imiazolidinone and 3.96 g of N-methyl-N-(trimethylsilyl)trifluoroacetamide (19.9 mol) in 50 ml of ethyl acetate was added dropwise. The reaction mixture was stirred overnight at ambient temperature, washed twice with brine, dried with sodium sulfate and evaporated in vacuo. The residue was dissolved in methanol/water and the pH adjusted to 6.5 by adding 1N sodium hydroxide. After evaporation of the methanol, the aqueous solution was freeze-dried (yield: 9.3 g; melting point 180° C., dec).
  • 9
  • [ 1189-71-5 ]
  • [ 114903-51-4 ]
  • [ 815-06-5 ]
  • [ 24589-78-4 ]
  • [ 59511-72-7 ]
  • (S)-[1-[ [[[(3,4-Dihydroxyphenyl)amino]sulfonyl]amino]carbonyl]-2-oxo-3-azetidinyl]carbamic acid, phenylmethyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
With hydrogenchloride; triethylamine; In (2S)-N-methyl-1-phenylpropan-2-amine hydrate; dichloromethane; ethyl acetate; (A) (S)-[1-[ [[[(3,4-Dihydroxyphenyl)amino]sulfonyl]amino]carbonyl]-2-oxo-3-azetidinyl]carbamic acid, phenylmethyl ester 16.27 g (81.7 mmol) of N-methyl-N-(trimethylsilyl)trifluoroacetamide was added to a solution of 9.76 g (40.8 mmol) of 4-amino-1,2-benzenediol, trifluoroacetate salt in 100 ml of ethyl acetate, and the mixture was stirred for one hour at room temperature. The solvent and most of the N-<strong>[815-06-5]methyltrifluoroacetamide</strong> were evaporated at 60 C. The residue was dissolved in 100 ml of ethyl acetate (solution A). To a suspension of 8.99 g (40.8 mmol) of (S)-(2-oxo-3-azetidinyl)carbamic acid, phenylmethyl ester in 100 ml of ethyl acetate was added 5.78 g (40.8 mmol) of chlorosulfonyl isocyanate, and the mixture was stirred for one hour at room temperature. After the addition of 100 ml of dichloromethane, the solution was cooled to 0 C. 16.52 g (163.3 mmol) of triethylamine and, subsequently, solution A were added. The resulting mixture was stirred overnight at room temperature. After addition of 200 ml of ice water, the pH was adjusted to 2 by adding 2N hydrochloric acid. The organic layer was separated and the aqueous phase extracted three times with ethyl acetate. The combined organic layers were washed with brine and dried over magnesium sulfate. The solvent was removed in vacuo and the residue triturated with petroleum ether; yield: 11.40 g.
  • 10
  • [ 1189-71-5 ]
  • [ 114903-53-6 ]
  • [ 24589-78-4 ]
  • [ 59511-72-7 ]
  • (S)-[1-[[[[2-[[(3,4-dihydroxyphenyl)amino]carbonyl]hydrazino]sulfonyl]amino]carbonyl]-2-oxo-3-azetidinyl]carbamic acid, phenylmethyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
With hydrogenchloride; triethylamine In dichloromethane; ethyl acetate 12.D (D) (D) (S)-[1-[[[[2-[[(3,4-Dihydroxyphenyl)amino]carbonyl]hydrazino]sulfonyl]amino]carbonyl]-2-oxo-3-azetidinyl]carbamic acid, phenylmethyl ester 2.93 ml (15.0 mmol) of N-methyl-N-trimethylsilyltrifluoroacetamide was added to a suspension of 1.10 g (5.0 mmol) of N-(3,4-dihydroxyphenyl)hydrazinecarboxamide, hydrochloride in 10 ml of dry ethyl acetate. After stirring for 1 hour at 50° C., the clear solution was evaporated in vacuo and the residue was redissolved in 10 ml of dry ethyl acetate (solution A). To a suspension of 1.10 g (5.0 mmol) of (S)-(2-oxo-3-azetidinyl)carbamic acid, phenylmethyl ester in 40 ml of dry ethyl acetate, 0.45 ml (5.00 mmol) of chlorosulfonyl isocyanate was added with stirring and the mixture was stirred for 1 hour at room temperature and then cooled to 0° C. After the addition of 10 ml of dry dichloromethane and 2.09 ml (15.0 mmol) of triethylamine, solution A was dropped in with stirring at 0° C. After stirring overnight at 0° C., the reaction mixture was poured into 10 ml of an ice cold buffer solution (citrate pH 2). The pH was maintained by the addition of 2N hydrochloric acid (pH=2). The organic layer was separated and the aqueous phase was extracted with ethyl acetate. The organic layers were combined, washed with brine, dried (magnesium sulfate) and evaporated in vacuo to leave a residue which became crystalline by stirring with a few ml of ethyl acetate. After diluting with dry ether, the precipitate was collected by suction, washed with ether and dried in vacuo; yield: 1.53 g, melting point 130° C. dec.
  • 11
  • [ 1189-71-5 ]
  • [ 1132-47-4 ]
  • [ 24589-78-4 ]
  • [ 59511-72-7 ]
  • (S)-[1-[[[[2-[(3,4-dihydroxyphenyl)acetyl]hydrazino]sulfonyl]amino]carbonyl]-2-oxo-3-azetidinyl]carbamic acid, phenylmethyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
With triethylamine In (2S)-N-methyl-1-phenylpropan-2-amine hydrate; dichloromethane; ethyl acetate 15.B (B) (B) (S)-[1-[[[[2-[(3,4-Dihydroxyphenyl)acetyl]hydrazino]sulfonyl]amino]carbonyl]-2-oxo-3-azetidinyl]carbamic acid, phenylmethyl ester 1.95 ml (10.0 mmol) of N-methyl-N-trimethylsilyltrifluoroacetamide (95%) was added to a suspension of 0.91 g (5.0 mmol) of 3,4-dihydroxyphenylacetylhydrazide in 15 ml of dry ethyl acetate. After stirring for 1 hour at 50°-55° C., the almost clear solution was evaporated in vacuo and the residue was dissolved in 10 ml of dry ethyl acetate (solution A). To a suspension of 1.10 g of (S)-(2-oxo-3-azetidinyl)carbamic acid, phenylmethyl ester (5.0 mmol) in 40 ml of dry ethyl acetate, 0.45 ml (5.0 mmol) of chlorosulfonyl isocyanate was added with stirring. The mixture was stirred for 1 hour at room temperature and then cooled to 0° C. After the dropwise addition of a solution of 2.09 ml (15.0 mmol) of triethylamine in 10 ml of dry dichloromethane and solution A, stirring was continued for 2.5 hours at 0° C. Ice water was added, and the organic layer was separated and washed successively with cold buffer solution (citrate pH 2) and brine. Drying (magnesium sulfate) and evaporation in vacuo gave a residue which solidified by stirring with ether; yield: 2.1 g.
  • 12
  • [ 1189-71-5 ]
  • [ 114875-05-7 ]
  • [ 24589-78-4 ]
  • [ 59511-72-7 ]
  • (S)-[1-[[[[[2-(aminocarbonyl)-4,5-dihydroxyphenyl]amino]sulfonyl]amino]carbonyl]-2-oxo-3-azeidinyl]carbamic acid, phenylmethyl ester [ No CAS ]
  • (E) (S)-[1-[[[[[2-(aminocarbonyl)-4,5-dihydroxyphenyl]amino]sulfonyl]amino]carbonyl]-2-oxo-3-azetidinyl]carbamic acid, phenylmethyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
With hydrogenchloride; triethylamine In dichloromethane; ethyl acetate; acetonitrile 19 (E) (S)-[1-[[[[[2-(aminocarbonyl)-4,5-dihydroxyphenyl]amino]sulfonyl]amino]carbonyl]- 2-oxo-3-azetidinyl]carbamic acid, phenylmethyl ester (E) (S)-[1-[[[[[2-(aminocarbonyl)-4,5-dihydroxyphenyl]amino]sulfonyl]amino]carbonyl]- 2-oxo-3-azetidinyl]carbamic acid, phenylmethyl ester To a suspension of 6.1 g (29.8 mmol) of 2-amino-4,5-dihydroxybenzamide, monohydrochloride in 240 ml of absolute acetonitrile was added 17.8 g (89.4 mmol) of N-methyl-N-(trimethylsilyl)trifluoroacetamide to obtain a blue solution. After some minutes, a precipitate was formed. The mixture was stirred for 30 minutes at room temperature and then evaporated to dryness a high vacuum for 60 minutes. The crystalline residue was dissolved in 360 ml of absolute ethyl acetate (solution A). To a suspension of 6.56 g (29.8 mmol) of (S)-(2-oxo-3-azetidinyl)carbamic acid, phenylmethyl ester in 120 ml of absolute ethyl acetate was added 4.22 g (29.8 mmol) of chlorosulfonyl isocyanate. After stirring for 1 hour, the solution was cooled to 0° C. and 90 l of dichloromethane and 9.05 g (89.4 mmol) of triethylamine were added. (Solution B). Solution B was added in four portions to solution A at 0° C. After stirring overnight at room temperature, ice was added, and after 30 minutes, the pH was brought to 2 with 3N hydrochloric acid. The phases were separated, the aqueous phase was extracted twice with ethyl acetate, and the combined organic phases were dried over magnesium sulfate. Evaporation and trituration of the residue with ether yielded 12.2 g of (S)-[1-[[[[[2-(aminocarbonyl)-4,5-dihydroxyphenyl]amino]sulfonyl]amino]carbonyl]-2-oxo-3-azeidinyl]carbamic acid, phenylmethyl ester.
  • 13
  • [ 1189-71-5 ]
  • [ 114875-19-3 ]
  • [ 815-06-5 ]
  • [ 24589-78-4 ]
  • [ 59511-72-7 ]
  • (S)-[1-[[[[2-[(3,4-dihydroxyphenyl)methylene]hydrazino]sulfonyl]amino]carbonyl]-2-oxo-3-azetidinyl]carbamic acid, phenylmethyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
With hydrogenchloride; triethylamine; In (2S)-N-methyl-1-phenylpropan-2-amine hydrate; dichloromethane; ethyl acetate; (C) (S)-[1-[[[[2-[(3,4-Dihydroxyphenyl)methylene]hydrazino]sulfonyl]amino]carbonyl]-2-oxo-3-azetidinyl]carbamic acid, phenylmethyl ester To a suspension of 7.99 g (30 mmol) of 4-(hydrazonomethyl)-1,2-benzenediol, trifluoroacetate salt in 60 ml of ethyl acetate were added 11.13 ml (60 mmol) of N-methyl-N-(trimethylsilyl)trifluoroacetamide and 4.18 ml (30 mmol) of triethylamine. The mixture was stirred for one hour at 60 C., and the solvent and most of the N-<strong>[815-06-5]methyltrifluoroacetamide</strong> were evaporated in vacuo at 60 C. The resulting residue was suspended in 45 ml of ethyl acetate (solution A). To a suspension of 6.61 g (30 mmol) of (S)-(2-oxo-3-azetidinyl)carbamic acid, phenylmethyl ester in 90 ml of ethyl acetate was added 2.62 ml (30 mmol) chlorosulfonyl isocyanate, and the mixture was stirred for one hour at room temperature. After the addition of 45 ml of dichloromethane, the solution was cooled to 0 C., and 12.54 ml (90 mmol) of triethylamine was added, followed by solution A. The mixture was stirred over the weekend at room temperature and the precipitate filtered off by suction. To the filtrate were added 100 ml of ice water, and the mixture was washed two times with ethyl acetate. The aqueous phase was adjusted to pH 2 by adding 2N hydrochloric acid and extracted three times with ethyl acetate. The organic layer was dried over magnesium sulfate, filtered and evaporated in vacuo. The residue was triturated with ether, filtered off by suction and dried in vacuo; yield: 5.58 g.
  • 14
  • [ 114875-49-9 ]
  • [ 24589-78-4 ]
  • [ 59511-72-7 ]
  • (S)-3-[[(Phenylmethoxy)carbonyl]amino]-N-[[2-(2,3-dihydroxybenzoyl)hydrazino]sulfonyl]-2-oxo-1-azetidinecarboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
In isopropyl alcohol; acetonitrile 26.F (F) (F) (S)-3-[[(Phenylmethoxy)carbonyl]amino]-N-[[2-(2,3-dihydroxybenzoyl)hydrazino]sulfonyl]-2-oxo-1-azetidinecarboxamide (2,3-Dihydroxybenzoyl)hydrazine, trifluoroacetate salt (2.82 g) was suspended in 50 ml of acetonitrile and 13.5 g of N-methyl-N-(trimethylsilyl)trifluoroacetamide were added. After stirring for one hour at 40° C., the solvent and trifluoroacetic acid, trimethylsilyl ester formed were distilled off in vacuo. The remaining oil was dissolved again in 50 ml of dried acetonitrile, cooled to 0° C. and added dropwise to a solution of 3.48 g of an adduct of chlorosulfonylisocyanate and (S)-(2-oxo-3-azetidinyl)carbamic acid, phenylmethyl ester in 100 ml of acetonitrile at 0° C. with stirring. After continuous stirring overnight, the solvent was distilled off in vacuo and the residue stirred (1 hour) with 200 ml of isopropanol. (S)-3-[[(Phenylmethoxy)carbonyl]amino]-N-[[2-(2,3-dihydroxybenzoyl)hydrazino]sulfonyl]-2-oxo-1-azetidinecarboxamide precipitated from the solution. Isolation by filtration and washing with ether yielded 3.87 g of white powder.
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