96034-57-0|(2S,4R)-4-Hydroxy-1-(((4-nitrobenzyl)oxy)carbonyl)pyrrolidine-2-carboxylic acid| Ambeed

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Quality Control of [ 96034-57-0 ] Purity: 98% SDS Specification

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Product Details of [ 96034-57-0 ]

CAS No. :	96034-57-0
Formula :	C₁₃H₁₄N₂O₇
M.W :	310.26
SMILES Code :	O=C(N1[C@H](C(O)=O)C[C@@H](O)C1)OCC2=CC=C([N+]([O-])=O)C=C2
MDL No. :	MFCD16294320
InChI Key :	JMJMJDNHVXYAOC-MNOVXSKESA-N
Pubchem ID :	10566895

Safety of [ 96034-57-0 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H315-H319-H335
Precautionary Statements:	P261-P280-P301+P312-P302+P352-P305+P351+P338

Application In Synthesis of [ 96034-57-0 ]

* 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 [ 96034-57-0 ]

[ 96034-57-0 ] Synthesis Path-Downstream 1~35

1
[ 96034-57-0 ]
[ 541-88-8 ]
[ 132984-58-8 ]

References: [1]Journal of the American Chemical Society,1959,vol. 81,p. 4364.

2
[ 51-35-4 ]
[ 4457-32-3 ]
[ 96034-57-0 ]

Yield	Reaction Conditions	Operation in experiment
93%		Example 4: Synthesis of (4R,5S,6S)- 3-[[(3S,5S)-5-[(dimethylamino)carbonyl]-3-ρyrrolidinyl]thio]-6-[(lR)-l-hydroxyethyl]-4-methyl- 7-oxo-l-azabicyclo[3,2,0]hept-2-ene-2-carboxylic acid (I)Synthesis of (2S,4S)-2-dimethylaminocarbonyl -4-thio-l-PNZ-pyrrolindine (XX)L-hydoxyproline (XXVI) (26.2 g, 0.20 mol) was added to a solution of sodium hydroxide (220 ml, 2N) and cooled to O0C to 50C. The solution of p-nitrobenzyl chloroformate dissolved in <n="17"/>methylene chloride (40 ml) was added dropwise. After stirred at the same temperature for 1 h, the phase of methylene chloride was separated. The aqueous phase was washed with methylene chloride (70 ml) and acidified with concentrated sulfuric acid (36.6 g) at a temperature of O0C to 5 C . Substantive crystals were precipitated, collected by filtration under vacuum, washed with water, dried, and afford trans- l-(p-nitrobenzyloxycarbonyl) -4-hydroxyl-L-proline (XXV) (57.8 g, yield 93%), m.p.: 134~135.5C.
93%		Example 6] Synthesis of (2S,4S)-2-dimethylaminocarbonyl -4-acetylthio-l-PNZ-pyrrolidine (XIX)1. Synthesis of trans- l-(p-nitrobenzyloxycarbonyl) -4-hydroxyl-L-proline (XV) L-hydoxyproline (XXVI) (26.2 g, 0.20 mol) was added to a solution of sodium hydroxide(220 ml, 2N) and cooled to 0C to 5C. The solution, of p-nitrobenzyl chloroformate dissolved in methylene chloride (40 ml) was added dropwise. After stirred at the same temperature for 1 h, the phase of methylene chloride was separated. The aqueous phase was washed with methylene chloride (70 ml) and acidified with concentrated sulfuric acid (36.6 g) at a temperature of 0C to 5 C . Substantive crystals were precipitated, collected by filtration under vacuum, washed with water, dried, and afford trans- l-(p-nitrobenzyloxycarbonyl) -4-hydroxyl-L-proline (XXV) (57.8 g, yield 93%), m.p.: 134~135.5C.
92.6%	With sodium hydroxide; In dichloromethane; water monomer; at 0 - 5℃; for 3h;	Add sodium hydroxide (66.9g, 1.68mol) and 600g of water to the reaction flask, after stirring and dissolving, add trans-L-hydroxyproline (100g, 0.76mol), stir and dissolve completely and then cool down to 0C, Add dropwise a solution of 50% p-nitrobenzyl chloroformate in dichloromethane (370 g, 0.86 mol), the temperature does not exceed 5 C; after the dropping is completed, the reaction is carried out at 0 to 5 C for 3 hours. The phases were extracted with 100 mL of dichloromethane; the aqueous phase was separated, and the pH was adjusted to 2-3 with 10% hydrochloric acid, then extracted three times with ethyl acetate (200 mL×3), and the organic phases were combined, washed with saturated brine, and washed with anhydrous sodium sulfate. It was dried, filtered, concentrated to dryness, and recrystallized with ethanol to obtain 219.2 g of white solid (intermediate 7) with a yield of 92.6%.

80%	With sodium hydroxide; In water monomer; toluene; at 0 - 20℃; for 2h;Inert atmosphere; Schlenk technique;	trans-4-Hydroxy-L-proline (SI, 1.0 g, 7.6 mmol, 1.0 eq.) was dissolved in aqueous NaOH (0.5 M, 34 mL) and cooled in an ice bath. At 0 - 5 C, 4-nitrobenzoylchloroformate (1.9 g, 8.6 mmol, 1.1 eq.) in toluene (25 mL) was added dropwise. The bi-phasic mixture was stirred for two hours, after which the toluene (30 mL) was added and the phases separated. The aqueous phase was extracted with toluene and the combined organic phases extracted with aqueous NaOH (0.5 M). The aqueous phases were combined, adjusted to pH = 1 by adding cone. HCI and extracted with ethyl acetate (3 times). The extract was dried over sodium sulfate, filtered and concentrated in vacuo. Thus, compound 1 (1.89 g, 6.1 mmol, 80%) was obtained as off-white solid. ESI-LRMS for Ci3Hi5N207+[MH+]: calcd. 311.1 found 311.2
		Trans-4-hydroxy-L-proline (II) was added to a solution of sodium hydroxide in water at 0-5 C, and stirred to get a clear solution, followed by p- nitrobenzyloxycarbonyl chloride in dichloromethane (MDC) was added and stirred till completion of reaction. at 0-5 C. To this reaction mass sodium hydroxide solution was added and the layers were separated. To the aqueous layer methanol was added and pH was adjusted to acidic using sulphuric acid at 0-5 C. The solid obtained was filtered, washed with water and dried in vacuum at 50C to afford the title compound (III) as colorless crystals.
31.95 kg	With sodium hydroxide; In dichloromethane; water monomer; at 0 - 5℃; for 5h;Large scale;	20L reactor water 12kg,1kg sodium hydroxide, stirred and dissolved, cooled to 25 ~ 30 ,Add L-hydroxyproline 15kg, stirring to dissolve,Cool to 0 ~ 5 ,The temperature was controlled at 0 ~ 5 2.7kg of p-nitrobenzyl chloroformate and 3kg of dichloromethane were added dropwise.Dropping about 2 hours, dropping is completed,Keep stirring 0 ~ 5 for about 3 hours. Detection reaction is complete.The dichloromethane phase was separated, the aqueous phase was washed with 3 kg of dichloromethane, the aqueous phase was separated,Control temperature but 15 degrees,Concentrated sulfuric acid adjusted to pH 2, cooled to 0 filtration,Washed, dried in the product(5) To a solution of (2S, 4R) -4- hydroxy- 1 - (((4-nitrobenzoyl) oxy) carbonyl) pyrrolidine-31.95kg
	With sodium hydroxide; In water monomer; toluene; at -5 - 0℃; for 1.25h;pH 9.0;	In a 500mL three-neck bottle added purified water 192g, add 15.3g of sodium hydroxide, stir and dissolve, and cool at 0 C; add 3g of 3-hydroxyproline, stir and dissolve; cool down at -5 C, added the drops of about 180g of p-nitrobenzyl chloroformate toluene solution, after about 1 hour, the drop is completed and pΗ=9; continue to stir for 15 minutes, and then let stand for 20 min, dispense, and obtained lower aqueous phase; in the lower aqueous phase added toluene 63mL X 3 and wash three times, stand still; control the internal temperature at 10 C, and add 6N hydrochloric acid to the aqueous phase, add dropwise until the water phase becomes turbid and stop adding, pH=4, add a small amount of seed crystals and stir until more crystals are precipitated, continue to add hydrochloric acid at pΗ = 2 (a total of about 5g of 6N dilute hydrochloric acid is required), cool down at 0 C, heat 1h suction filtration, wash with pure water to pΗ = 3, obtained compound I hydrate product.

References: [1]Bioorganic and Medicinal Chemistry Letters,2000,vol. 10,p. 95 - 99.
[2]Patent: WO2007/104219,2007,A1 .Location in patent: Page/Page column 15-16.
[3]Patent: WO2007/104221,2007,A1 .Location in patent: Page/Page column 18.
[4]Patent: CN114163371,2022,A .Location in patent: Paragraph 0162; 0197-0199.
[5]Journal of the Chemical Society. Perkin transactions I,1997,p. 503 - 509.
[6]Organic Process Research and Development,2003,vol. 7,p. 649 - 654.
[7]Patent: WO2021/94410,2021,A1 .Location in patent: Page/Page column 3; 37-38.
[8]ChemBioChem,2013,vol. 14,p. 499 - 509.
[9]Journal of the American Chemical Society,1952,vol. 74,p. 3818,3819.
[10]Archiv der Pharmazie,1999,vol. 332,p. 111 - 114.
[11]Patent: WO2011/141847,2011,A1 .Location in patent: Page/Page column 7-9.
[12]Patent: CN104130262,2017,B .Location in patent: Paragraph 0123; 0124; 0125.
[13]Patent: CN109134337,2019,A .Location in patent: Paragraph 0048-0050; 0055-0057.

3
[ 96034-57-0 ]
[ 124-63-0 ]
(2S,4R)-4-Methanesulfonyloxy-2-methanesulfonyloxycarbonyl-pyrrolidine-1-carboxylic acid 4-nitro-benzyl ester [ No CAS ]

References: [1]Heterocycles,1995,vol. 41,p. 147 - 160.

4
[ 96034-57-0 ]
[ 108-23-6 ]
(2S,4R)-4-Hydroxy-2-isopropoxycarbonyloxycarbonyl-pyrrolidine-1-carboxylic acid 4-nitro-benzyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine; In dichloromethane; at -15℃; for 0.5h;Inert atmosphere;	Under nitrogen protection,(5) To a solution of (2S, 4R) -4- hydroxy- 1 - (((4-nitrobenzyl) oxy) carbonyl)31.3 g was dissolved in 300 mL of methylene chloride,Triethylamine 12.1g,Stirring and cooling to -15 C, isopropyl chloroformate 13.5g,The reaction was stirred at this temperature for 30 minutes. 16.2 g of triethylamine was added,At this temperature methyl methanesulfonyl chloride 16g was added dropwise,Stir at this temperature for 30 minutes. Triethylamine 25.3g,Add 10.2 g of sodium sulfide solution in 100 mL.The reaction was carried out at 5-10 C for 1 hour. The reaction was completed, washed with 1N hydrochloric acid 300mL once,Washed with saturated brine 300mL once,The aqueous phase was combined once with 200 mL of dichloromethane. Dried over anhydrous sodium sulfate,Filtration, the filtrate was concentrated crystallization20.2 g of 4-nitro (1S, 4S) -3-oxo-2-thia-5-azabicyclo [2.2.1] heptane-5-carboxylic anhydride (3)
	With triethylamine; In dichloromethane; at -20℃; for 0.283333h;	1) Add 1.8g of M1 to 33mL of dichloromethane,Keep the liquid temperature at -20 C and then add 0.85g of isopropyl chloroformateThen add 0.82g TEA dropwise,Reaction for 17min.
	With triethylamine; In dichloromethane; at -16℃; for 0.25h;	1) Add 1.8g M to 32mL dichloromethane1 (ie, [(2S, 4R)-2-carboxy-1-(4-nitrobenzyloxycarbonyl)pyrrolidine)]),Keep the liquid temperature at -16C, first add 0.71g isopropyl chloroformate, then 0.76g TEA, and react for 15min;

With triethylamine; In dichloromethane; at -10 - 0℃; for 2h;Inert atmosphere;

Under nitrogen protection, intermediate 7 (30g, 0.10mol), triethylamine (27.9g, 0.28mol) and dichloromethane 500mL were added to the reaction flask, cooled to -10C, and isopropyl chloroformate (13.1 mol) was added dropwise. g, 0.11mol), the temperature does not exceed 0 C, after the dripping is completed, react at 0 C for 2 hours, cool down to -10 C, add methanesulfonyl chloride (15.0g, 0.13mol) dropwise, the temperature does not exceed 0 C, after dropping The reaction was carried out at 0 C for 2 h to obtain a product containing intermediate 8. To the obtained product containing intermediate 8, an aqueous solution of dimethylamine with a mass concentration of 40% (14.2 g, 0.13 mol) was added dropwise, and the temperature did not exceed 10 C. After the reaction was completed, the reaction was incubated for 3 hours. After the reaction was completed, washed with 300 mL of 2% dilute hydrochloric acid, washed with 300 mL of 5% potassium carbonate, washed with water and saturated brine, separated the organic layer, dried over anhydrous sodium sulfate, filtered, and concentrated to dryness. Recrystallization from methanol gave 29.8 g of yellow solid powder (intermediate 9) with a yield of 74.2%.

References: [1]Heterocycles,1995,vol. 41,p. 147 - 160.
[2]Patent: CN104130262,2017,B .Location in patent: Paragraph 0126; 0127; 0128.
[3]Patent: CN110386942,2019,A .Location in patent: Paragraph 0028-0029; 0033-0034; 0038-0039; 0043-0044; 0048.
[4]Patent: CN111592555,2020,A .Location in patent: Paragraph 0022-0023; 0027-0028; 0032-0033.
[5]Patent: CN114163371,2022,A .Location in patent: Paragraph 0162; 0197; 0200-0201.

5
[ 96034-57-0 ]
[ 62-53-3 ]
[ 188578-74-7 ]

References: [1]Journal of the Chemical Society. Perkin transactions I,1997,p. 503 - 509.

6
[ 96034-57-0 ]
[ 543-27-1 ]
C₁₈H₂₂N₂O₈ [ No CAS ]

References: [1]Journal of the Chemical Society. Perkin transactions I,1997,p. 503 - 509.

7
[ 67-56-1 ]
[ 96034-57-0 ]
[ 101803-29-6 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2000,vol. 10,p. 95 - 99.
[2]Archiv der Pharmazie,1999,vol. 332,p. 111 - 114.
[3]Organic Process Research and Development,2003,vol. 7,p. 649 - 654.

8
[ 96034-57-0 ]
[ 104795-10-0 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2000,vol. 10,p. 95 - 99.

9
[ 96034-57-0 ]
[ 117811-69-5 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2000,vol. 10,p. 95 - 99.

10
[ 96034-57-0 ]
[ 137049-21-9 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2000,vol. 10,p. 95 - 99.

11
[ 96034-57-0 ]
(6S,7aS)-6-Mercapto-3,3-dimethyl-hexahydro-pyrrolo[1,2-c]imidazol-1-one [ No CAS ]