[ CAS No. 5680-83-1 ] {[proInfo.proName]}

Name: 5680-83-1|Benzyl (2-hydrazinyl-2-oxoethyl)carbamate|97%
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SKU: A631354
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Quality Control of [ 5680-83-1 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

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Product Details of [ 5680-83-1 ]

CAS No. :	5680-83-1	MDL No. :	MFCD00025127
Formula :	C₁₀H₁₃N₃O₃	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	FBXJOIKPPWLCJU-UHFFFAOYSA-N
M.W :	223.23	Pubchem ID :	72771
Synonyms :

Safety of [ 5680-83-1 ]

Signal Word:	Warning	Class:
Precautionary Statements:	P261-P264-P270-P271-P280-P302+P352-P304+P340-P305+P351+P338-P312-P330-P362-P403+P233-P501	UN#:
Hazard Statements:	H302-H312-H332	Packing Group:
GHS Pictogram:

Application In Synthesis of [ 5680-83-1 ]

* 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 [ 5680-83-1 ]

[ 5680-83-1 ] Synthesis Path-Downstream 1~54

1
[ 5680-83-1 ]
[ 23262-07-9 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride; acetic acid; sodium nitrite Behandeln einer Loesung des Reaktionsprodukts in Aether mit L-Alanin-aethylester;
	Multi-step reaction with 2 steps 1: p-toluenesulfonic acid / methanol / 16 h / 20 °C 2: 92 percent / Et₃N / tetrahydrofuran / 1.33 h / Heating

Reference： [1]Erlanger; Brand [Journal of the American Chemical Society, 1951, vol. 73, p. 3508]
[2]Kashima, Choji; Tsuruoka, Shiro; Mizuhara, Saori [Heterocycles, 2000, vol. 52, # 1, p. 413 - 424]

2
[ 5680-83-1 ]
[ 50622-95-2 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride; acetic acid; sodium nitrite
	With hydrogenchloride; acetic acid; sodium nitrite In water at -5℃;
	With hydrogenchloride; sodium nitrite In chloroform; water at 4℃; for 0.25h;

With hydrogenchloride; sodium nitrite In water for 0.0833333h;

Reference： [1]Erlanger; Brand [Journal of the American Chemical Society, 1951, vol. 73, p. 3508]
[2]Luk'yanenko, N. G.; Bogat-skii, A. V.; Basok, S. S.; Ostrovskaya, L. K.; Nazarova, N. Yu.; Karpenko, L. P. [Journal of Organic Chemistry USSR (English Translation), 1984, vol. 20, # 7, p. 1438 - 1444][Zhurnal Organicheskoi Khimii, 1984, vol. 20, # 7, p. 1580 - 1587]
[3]Kawasaki; Maeda; Watanabe; Kaneto [Chemical and Pharmaceutical Bulletin, 1988, vol. 36, # 5, p. 1766 - 1771]
[4]Okada, Yoshio; Tsuda, Yuko; Yagyu, Masami [Chemical and pharmaceutical bulletin, 1980, vol. 28, # 7, p. 2254 - 2258]

3
[ 5680-83-1 ]
[ 64532-71-4 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride; acetic acid; sodium nitrite Behandeln einer Loesung des Reaktionsprodukts in Aether mit D-Alanin-aethylester;

Reference： [1]Erlanger; Brand [Journal of the American Chemical Society, 1951, vol. 73, p. 3508]

4
[ 1212-53-9 ]
[ 5680-83-1 ]

Yield	Reaction Conditions	Operation in experiment
69%	With hydrazine hydrate; In ethanol; for 3h;Reflux;	General procedure: The ester (10.0 mmol) was added in small portions to a solution of hydrazinehydrate (40.0 mmol) in 3.0 mL of ethanol. After refluxing for 3?6.5 h, the residuewas concentrated in vacuum and purified by column chromatography.

Reference： [1]Tetrahedron Letters,1995,vol. 36,p. 6591 - 6594
[2]Beilstein Journal of Organic Chemistry,2016,vol. 12,p. 2865 - 2872
[3]Beilstein Journal of Organic Chemistry,2017,vol. 13,p. 2596 - 2602
[4]Chemical Communications,2012,vol. 48,p. 5772 - 5774
[5]Journal of Biological Chemistry,1951,vol. 188,p. 251,260

5
[ 1145-81-9 ]
[ 5680-83-1 ]

Reference： [1]Journal of the American Chemical Society,1951,vol. 73,p. 3508
[2]Heterocycles,2000,vol. 52,p. 413 - 424

6
[ 6096-81-7 ]
[ 5680-83-1 ]
[ 101587-22-8 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride; sodium nitrite In diethyl ether; acetic acid

Reference： [1]Dyer,E.; Shyluk,S. [Journal of Organic Chemistry, 1961, vol. 26, p. 1321 - 1323]

7
[ 1138-80-3 ]
[ 5680-83-1 ]

Yield	Reaction Conditions	Operation in experiment
57%	Stage #1: N-(Benzyloxycarbonyl)glycine With 4-methyl-morpholine; chloroformic acid ethyl ester In tetrahydrofuran at 20℃; for 2h; Stage #2: With hydrazine In tetrahydrofuran at 0 - 20℃;	112.1 Cbz-glycine (30 g, 143 mmol), 4-methylmorpholine (18.8 g, 185 mmol) and ethyl chloroformate (17 g, 157 mmol) were dissolved in THF (500 mL) and stirred at RT for 2 hours. The mixture was filtered in order to remove the white precipitate. The filtrate was cooled at 00C and hydrazine (35.8 g, 715 mmol) in THF (50 mL) was added. The mixture was stirred at RT overnight. Saturated NaHCO3 was added and the mixture was extracted with EtOAc. The organic layer was washed with brine, dried over MgSO4, filtered, concentrated and dried under vacuum to give a white solid (18.3 g, 57%). 1H NMR (400 MHz, CDCl3): δ 7.28-7.38 (m, 5H), 5.10 (s, 2H), 3.82 (s, 2H); LC/MS: m/e = 224 (M+H)+.
	(i) HCl, MeOH, (ii) N₂H₄*H₂O; Multistep reaction;
	With hydrazine hydrate monohydrate; triethylamine; fluoro-N,N,N',N'-tetramethylformamidinium hexafluorophosphate In N,N-dimethyl-formamide at 0 - 20℃; for 0.833333h;

	Multi-step reaction with 2 steps 1: DCC 2: N₂H₄*H₂O
	Multi-step reaction with 2 steps 1.1: N-[3-(N,N-dimethylamino)-propyl]-N'-ethyl-carbodiimide hydrochloride / dichloromethane / 0.5 h / 20 °C 1.2: 18 h / 20 °C 2.1: hydrogenchloride / dichloromethane; 1,4-dioxane
	Multi-step reaction with 2 steps 1: Sodium hydrogenocarbonate / N,N-dimethyl-formamide / 46 h / 20 °C / Inert atmosphere 2: hydrazine hydrate monohydrate / ethanol / 3 h / Reflux
	Multi-step reaction with 2 steps 1: Sodium hydrogenocarbonate / N,N-dimethyl-formamide / 46 h / 20 °C 2: hydrazine hydrate monohydrate / ethanol / Reflux
	Multi-step reaction with 2 steps 1: thionyl chloride / Inert atmosphere 2: hydrazine hydrate monohydrate / methanol / 12 h / 20 °C / Inert atmosphere
	Multi-step reaction with 2 steps 1: 1-propanephosphonic acid cyclic anhydride; N-ethyl-N,N-diisopropylamine / ethyl acetate / 3 h / 0 - 25 °C 2: hydrogenchloride / 1,4-dioxane / 2 h / 25 °C

Reference： [1]Current Patent Assignee: SUMITOMO CHEMICAL COMPANY LIMITED; Sumitomo Pharma (in: Sumitomo Chemical); Sumitomo Chemical (w/o Dongwoo Fine-Chem) - WO2010/114971, 2010, A1 Location in patent: Page/Page column 185-186
[2]Wolman,Y. et al. [Journal of the American Chemical Society, 1962, vol. 84, p. 1889 - 1892]
[3]El-Faham; Abdul-Ghani [Organic Preparations and Procedures International, 2003, vol. 35, # 4, p. 369 - 374]
[4]Ito,H. [Synthesis, 1979, p. 465 - 467]
[5]Damalanka, Vishnu C.; Kim, Yunjeong; Alliston, Kevin R.; Weerawarna, Pathum M.; Galasiti Kankanamalage, Anushka C.; Lushington, Gerald H.; Mehzabeen, Nurjahan; Battaile, Kevin P.; Lovell, Scott; Chang, Kyeong-Ok; Groutas, William C. [Journal of Medicinal Chemistry, 2016, vol. 59, # 5, p. 1899 - 1913]
[6]Barreto, Angélica De Fátima S.; Dos Santos, Veronica Alves; Andrade, Carlos Kleber Z. [Beilstein Journal of Organic Chemistry, 2016, vol. 12, p. 2865 - 2872]
[7]De Fátima Barreto, Angélica S.; Dos Santos, Veronica Alves; Zandrade, Carlos Kleber [Beilstein Journal of Organic Chemistry, 2017, vol. 13, p. 2596 - 2602]
[8]Bond, Andrew D.; Hanby, Abigail R.; King, Thomas A.; Moss, Thomas A.; Sore, Hannah F.; Spring, David R.; Stewart, Hannah L. [Chemical Communications, 2020, vol. 56, # 50, p. 6818 - 6821]
[9]Current Patent Assignee: ROCHE HOLDING AG - WO2022/43374, 2022, A1

8
[ 5680-83-1 ]
[ 91641-80-4 ]
[ 113398-28-0 ]

Yield	Reaction Conditions	Operation in experiment
69%	In acetonitrile for 18h; Heating;

Reference： [1]Sikorski, James A.; Mischke, Deborah A.; Schulte, Brett J. [Journal of Heterocyclic Chemistry, 1987, vol. 24, p. 1189 - 1197]

9
[ 5680-83-1 ]
[ 40149-90-4 ]
[ 77437-38-8 ]

Yield	Reaction Conditions	Operation in experiment
73%	With hydrogenchloride; triethylamine; sodium nitrite In N,N-dimethyl-formamide at -10℃; for 17h;

Reference： [1]Deak, Gy.; Gall-Istok, K.; Zara-Kaczian, E.; Kisfaludy, L. [Acta Chimica Academiae Scientiarum Hungaricae, 1980, vol. 104, # 4, p. 375 - 384]

10
[ 5680-83-1 ]
[ 49691-59-0 ]
[ 54321-69-6 ]

Yield	Reaction Conditions	Operation in experiment
	With acetic acid In ethanol for 6h; Ambient temperature;

Reference： [1]Hirai; Fujishita; Ishiba; Sugimoto; Matsutani; Tsukinoki; Hirose [Journal of Medicinal Chemistry, 1982, vol. 25, # 12, p. 1466 - 1473]

11
[ 5680-83-1 ]
[ 83520-07-4 ]
[ 83520-05-2 ]

Yield	Reaction Conditions	Operation in experiment
33%	With acetic acid In ethanol for 14h; Ambient temperature;

Reference： [1]Hirai; Fujishita; Ishiba; Sugimoto; Matsutani; Tsukinoki; Hirose [Journal of Medicinal Chemistry, 1982, vol. 25, # 12, p. 1466 - 1473]

12
[ 5680-83-1 ]
[ 54567-69-0 ]
[ 83520-05-2 ]

Yield	Reaction Conditions	Operation in experiment
17%	With acetic acid In ethanol for 6h; Ambient temperature;

Reference： [1]Hirai; Fujishita; Ishiba; Sugimoto; Matsutani; Tsukinoki; Hirose [Journal of Medicinal Chemistry, 1982, vol. 25, # 12, p. 1466 - 1473]

13
[ 2185-00-4 ]
[ 5680-83-1 ]
Z-Gly-NH-NH-CO-CH₂-NH₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With acetic acid

Reference： [1]Brenner,M.; Hofer,W. [Helvetica Chimica Acta, 1961, vol. 44, p. 1798 - 1801]

14
[ 5680-83-1 ]
[ 583-47-1 ]
[ 95317-10-5 ]

Reference： [1]Helvetica Chimica Acta,1961,vol. 44,p. 1798 - 1801

15
[ 5680-83-1 ]
[ 14825-82-2 ]
[ 94310-08-4 ]

Reference： [1]Helvetica Chimica Acta,1961,vol. 44,p. 1798 - 1801

16
[ 5680-83-1 ]
[ 5680-82-0 ]
[ 3916-37-8 ]

Yield	Reaction Conditions	Operation in experiment
	With N-Bromosuccinimide; triethylamine In tetrahydrofuran

Reference： [1]Wolman,Y. et al. [Journal of the American Chemical Society, 1961, vol. 83, p. 1263 - 1264]

17
[ 5680-83-1 ]
(S)-2-Amino-3-phenyl-propionic acid ethyl ester; hydrobromide [ No CAS ]
[ 3956-78-3 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrazine hydrate

Reference： [1]Wolman,Y. et al. [Journal of the American Chemical Society, 1961, vol. 83, p. 1263 - 1264]

18
[ 5680-83-1 ]
[ 431-03-8 ]
(5,6-Dimethyl-[1,2,4]triazin-3-ylmethyl)-carbamic acid benzyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
40%	With ammonium acetate In acetic acid Heating;

Reference： [1]Fan, Wen-Hong; Parikh, Mamta; Snyder, John K. [Tetrahedron Letters, 1995, vol. 36, # 37, p. 6591 - 6594]

19
[ 5680-83-1 ]
[ 134-81-6 ]
[ 21134-80-5 ]

Yield	Reaction Conditions	Operation in experiment
64%	With ammonium acetate In acetic acid Heating;

Reference： [1]Fan, Wen-Hong; Parikh, Mamta; Snyder, John K. [Tetrahedron Letters, 1995, vol. 36, # 37, p. 6591 - 6594]

20
[ 64-17-5 ]
[ 1145-81-9 ]
[ 7803-57-8 ]
[ 5680-83-1 ]

Reference： [1]Monatshefte fur Chemie,1951,vol. 82,p. 799,809, 812

21
[ 85-44-9 ]
[ 5680-83-1 ]
[ 439916-75-3 ]

Yield	Reaction Conditions	Operation in experiment
87%
80%	In toluene for 3h; Heating;

Reference： [1]Brosse, Nicolas; Grandeury, Arnaud; Jamart-Grégoire, Brigitte [Tetrahedron Letters, 2002, vol. 43, # 11, p. 2009 - 2011]
[2]Brosse, Nicolas; Pinto, Maria-Fatima; Jamart-Gregoire, Brigitte [European Journal of Organic Chemistry, 2003, # 24, p. 4757 - 4764]

22
[ 5680-83-1 ]
[ 131021-87-9 ]
L-aspartyl-azaglycyl-retro(CH₃NH)glycine benzyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
95%	In diethyl ether at 20℃; for 24h;

Reference： [1]Burger, Klaus; Lange, Torsten; Rudolph, Martin [Heterocycles, 2003, vol. 59, # 1, p. 189 - 198]

23
[ 82-07-5 ]
[ 5680-83-1 ]
N-(benzyloxycarbonylglycyl)-N'-(xanthen-9-ylcarbonyl)hydrazine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine; fluoro-N,N,N',N'-tetramethylformamidinium hexafluorophosphate In N,N-dimethyl-formamide at 0 - 20℃; for 2.5h;

Reference： [1]El-Faham; Abdul-Ghani [Organic Preparations and Procedures International, 2003, vol. 35, # 4, p. 369 - 374]

24
[ 5680-83-1 ]
[ 1026822-84-3 ]
N'-{3-[2-(4-fluorophenyl)-thiazol-4-yl]-2-mercaptopropanoyl}-N"-(N-benzyloxycarbonyl)-glycyl hydrazine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
75%	In acetonitrile at 20℃;

Reference： [1]Pumpor, Ksenia; Windeisen, Elisabeth; Burger, Klaus [Journal of Heterocyclic Chemistry, 2003, vol. 40, # 3, p. 435 - 442]

25
[ 5680-83-1 ]
[ 69-72-7 ]
N-(benzyloxycarbonylglycyl)-N'-salicylhydrazine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine; fluoro-N,N,N',N'-tetramethylformamidinium hexafluorophosphate In N,N-dimethyl-formamide at 0 - 20℃; for 2.5h;

Reference： [1]El-Faham; Abdul-Ghani [Organic Preparations and Procedures International, 2003, vol. 35, # 4, p. 369 - 374]

26
[ 5680-83-1 ]
[ 123-54-6 ]
[ 87023-85-6 ]

Yield	Reaction Conditions	Operation in experiment
	With toluene-4-sulfonic acid In methanol at 20℃; for 16h;

Reference： [1]Kashima, Choji; Tsuruoka, Shiro; Mizuhara, Saori [Heterocycles, 2000, vol. 52, # 1, p. 413 - 424]

27
[ 5680-83-1 ]
[ 17942-42-6 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: p-toluenesulfonic acid / methanol / 16 h / 20 °C 2: 67 percent / Et₃N / tetrahydrofuran / 1.33 h / Heating 3: hydrazine hydrate / methanol / 1.33 h / Heating
	Multi-step reaction with 2 steps 1: N₂H₄H₂O 2: N₂H₄H₂O

Reference： [1]Kashima, Choji; Tsuruoka, Shiro; Mizuhara, Saori [Heterocycles, 2000, vol. 52, # 1, p. 413 - 424]
[2]Wolman,Y. et al. [Journal of the American Chemical Society, 1961, vol. 83, p. 1263 - 1264]

28
[ 5680-83-1 ]
N'-(benzyloxycarbonyl)-N^β-(tert-butyloxycarbonyl)-N^α-methylglycinehydrazide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1.1: 80 percent / toluene / 3 h / Heating 2.1: 88 percent / DIAD; PPh₃ / tetrahydrofuran / 0.5 h / 20 °C 3.1: methylamine / methanol; tetrahydrofuran / 20 °C 3.2: 84 percent / DMAP / tetrahydrofuran / 20 °C 4.1: 91 percent / Mg(ClO₄)2 / acetonitrile / 3 h / 20 °C