Name: 21222-05-9|Bis(3-nitrophenyl)methanone|97%
Brand: Ambeed
SKU: A799232
Rating: 95 (30 reviews)

1
[ 119-61-9 ]
[ 21222-05-9 ]

Yield	Reaction Conditions	Operation in experiment
90%	With sulfuric acid; nitric acid at 75℃; for 0.5h;
	With sulfuric acid; nitric acid
8 g	With sulfuric acid; nitric acid at 85℃; for 4h;

	With sulfuric acid; nitric acid at 75℃; for 0.5h;
	With sulfuric acid; nitric acid at 60℃; for 2h;
	With sulfuric acid; nitric acid at 60℃; for 2h;
	With sulfuric acid; nitric acid at 75℃; for 1h;	9 Compound 11 To a mixture of 11-1 (10.0 g, 54.9 mmol) in H2S04 (50.0 mL) was added HNO3 (5.0 mL) in one portion. The mixture heated to 75 °C and then maintained at 75 °C for 1 h. The mixture was cooled to RT and then poured onto crushed ice. The gummy mass that formed hardened was mechanically broken up and washed with water until the washings were neutral. The filtrate cake was air dried and recrystallized from butanone (73 mL). A solid slowly formed overnight, which was filtered and then washed cool with butanone followed by cold EtOH to give 11-2 (12.10 g, crude) as a yellow solid.

Reference： [1]Mussons, Luisa; Raposo, Cesar; Anaya, Josefa; Grande, Manuel; Moran, Joaquin R.; Caballero, Cruz [Journal of the Chemical Society. Perkin transactions I, 1992, # 22, p. 3125 - 3128]
[2]Barnett; Matthews [Journal of the Chemical Society, 1924, vol. 125, p. 767]
[3]Renuka; Fredrick; Saravanan; Srinivasan [Indian Journal of Chemistry, Section A: Inorganic, Physical, Theoretical and Analytical, 2001, vol. 40, # 2, p. 175 - 181]
[4]Hejaz, Hatem A. M.; Woo, L. W. Lawrence; Purohit, Atul; Reed, Michael J.; Potter, Barry V. L. [Bioorganic and Medicinal Chemistry, 2004, vol. 12, # 10, p. 2759 - 2772]
[5]Location in patent: scheme or table Majumdar; Chakravorty, Santanu; Sinha, Randhir Kumar; Pal, Nilasish [Molecular Crystals and Liquid Crystals, 2009, vol. 515, p. 125 - 134]
[6]Location in patent: scheme or table Majumdar; Ghosh; Chakravorty [Molecular Crystals and Liquid Crystals, 2010, vol. 533, p. 63 - 72]
[7]Current Patent Assignee: JOHNSON & JOHNSON INC - WO2016/145103, 2016, A1 Location in patent: Paragraph 0228

2
[ 119-61-9 ]
[ 21222-05-9 ]
[ 51727-42-5 ]

Yield	Reaction Conditions	Operation in experiment
	With nitric acid

Reference： [1]Staedel [Justus Liebigs Annalen der Chemie, 1878, vol. 194, p. 347,369][Justus Liebigs Annalen der Chemie, 1883, vol. 218, p. 344]

3
[ 21222-05-9 ]
[ 303756-75-4 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydroxide; ethanol; hydroxylamine hydrochloride
	With hydroxylamine hydrochloride In pyridine Heating;

Reference： [1]Muenchmeyer [Chemische Berichte, 1887, vol. 20, p. 509]
[2]Smith,P.A.S.; Robertson,J.E. [Journal of the American Chemical Society, 1962, vol. 84, p. 1197 - 1204]

4
[ 21222-05-9 ]
[ 51339-33-4 ]

Yield	Reaction Conditions	Operation in experiment
88%	With sodium tetrahydroborate In methanol for 1h;
	With aluminum isopropoxide; isopropyl alcohol
	With sodium tetrahydroborate In methanol

With sodium tetrahydroborate In ethanol for 0.5h; Reflux;

Reference： [1]Subra, Gilles; Amblard, Muriel; Martinez, Jean [Tetrahedron Letters, 2002, vol. 43, # 50, p. 9221 - 9223]
[2]Stewart; Smith [Journal of the American Chemical Society, 1957, vol. 79, p. 5457,5459] Deno et al. [Journal of the American Chemical Society, 1955, vol. 77, p. 3044,3049][Journal of Organic Chemistry, 1954, vol. 19, p. 155,160]
[3]Mindl,J.; Vecera,M. [Collection of Czechoslovak Chemical Communications, 1973, vol. 38, p. 3496 - 3505]
[4]Jereb, Marjan; Vrazic, Dejan [Organic and Biomolecular Chemistry, 2013, vol. 11, # 12, p. 1978 - 1999]

5
[ 21222-05-9 ]
[ 611-79-0 ]

Yield	Reaction Conditions	Operation in experiment
5.8 g	With iron; ammonium chloride; In ethanol; water; at 80℃; for 4h;Inert atmosphere;	To a mixture of 11-2 (9.1 g, 33.4 mmol) in EtOH (30.0 mL) and H20 (30.0 mL) was added Fe (7.5 g, 133.7 mmol) and NH4C1 (8.9 g, 167.2 mmol) in one portion under N2. The mixture was stirred at 80 C for 4 h and filtered. The filtrate was poured into ice:water (w:w = 1 : 1) (50 mL) and stirred for 2 mins. The aqueous phase was extracted with EA (3 x 100 mL). The combined organic phase was washed with brine (2 x 80 mL), dried with anhydrous Na2S04, filtered and concentrated under reduced pressure. The residue was purified by silica gel chromatography (100-200 mesh silica gel, PE:EA = 1 :0-2: 1) and gave 11-3 (5.80 g) as a yellow solid

Reference： [1]Synlett,2004,p. 1835 - 1837
[2]Journal of the American Chemical Society,1992,vol. 114,p. 9959 - 9969
[3]Justus Liebigs Annalen der Chemie,1907,vol. 354,p. 198
Chemische Berichte,1905,vol. 38,p. 2764
[4]Justus Liebigs Annalen der Chemie,1849,vol. 72,p. 280
[5]Chemische Berichte,1894,vol. 27,p. 2296
[6]Arzneimittel-Forschung/Drug Research,1958,vol. 8,p. 532,536
[7]Justus Liebigs Annalen der Chemie,1878,vol. 194,p. 347,369
Justus Liebigs Annalen der Chemie,1883,vol. 218,p. 344
[8]Russian Journal of Applied Chemistry,1998,vol. 71,p. 2171 - 2176
[9]Molecular Crystals and Liquid Crystals,2009,vol. 515,p. 125 - 134
[10]Molecular Crystals and Liquid Crystals,2010,vol. 533,p. 63 - 72
[11]Patent: WO2016/145103,2016,A1 .Location in patent: Paragraph 0229

6
[ 4164-43-6 ]
[ 21222-05-9 ]

Yield	Reaction Conditions	Operation in experiment
	With water; chromic acid; acetic acid

Reference： [1]Gattermann; Ruedt [Chemische Berichte, 1894, vol. 27, p. 2296] Baeyer [Justus Liebigs Annalen der Chemie, 1907, vol. 354, p. 198][Chemische Berichte, 1905, vol. 38, p. 2764]

7
[ 180407-30-1 ]
[ 21222-05-9 ]

Yield	Reaction Conditions	Operation in experiment
	With chromium(VI) oxide; acetic acid

Reference： [1]Haskelberg; Lavie [Journal of Organic Chemistry, 1949, vol. 14, p. 498,500]

8
[ 21222-05-9 ]
[ 146028-45-7 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogen sulfide In hydrogen fluoride
	With Lawessons reagent In toluene at 110℃;

Reference： [1]Elofson,R.M. et al. [Journal of Organic Chemistry, 1964, vol. 29, p. 1355 - 1357]
[2]Mussons, Luisa; Raposo, Cesar; Anaya, Josefa; Grande, Manuel; Moran, Joaquin R.; Caballero, Cruz [Journal of the Chemical Society. Perkin transactions I, 1992, # 22, p. 3125 - 3128]

9
[ 21222-05-9 ]
[ 542-92-7 ]
6,6-Bis-<3-nitro-phenyl>-fulven [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sodium methylate

Reference： [1]Kresze,G. et al. [Justus Liebigs Annalen der Chemie, 1961, vol. 648, p. 51 - 56]

10
[ 21222-05-9 ]
[ 74-86-2 ]
[ 28437-49-2 ]

Yield	Reaction Conditions	Operation in experiment
	(i) Li, liq. NH₃, (ii) /BRN= 1888002/; Multistep reaction;

Reference： [1]Ried,W.; Neidhardt,R. [Chemische Berichte, 1970, vol. 103, p. 2208 - 2224]

11
[ 67-56-1 ]
[ 21222-05-9 ]
[ 116545-05-2 ]

Yield	Reaction Conditions	Operation in experiment
90%	With trifluorormethanesulfonic acid; trimethyl orthoformate In nitromethane for 4h; Heating;

Reference： [1]Thurkauf, Andrew; Jacobson, Arthur E.; Rice, Kenner C. [Synthesis, 1988, # 3, p. 233 - 234]

12
[ 119-61-9 ]
[ 21222-05-9 ]
[ 1033-26-7 ]
[ 51727-42-5 ]
[ 60191-42-6 ]
[ 1469-74-5 ]

Yield	Reaction Conditions	Operation in experiment
	With nitric acid at 90℃; for 3h; variation of condition; addition of H₂SO₄, also in CH₂Cl₂;

Reference： [1]Onopchenko, Anatoli; Sabourin, Edward T.; Selwitz, Charles M. [Journal of Organic Chemistry, 1981, vol. 46, # 24, p. 5014 - 5017]

13
[ 119-61-9 ]
[ 21222-05-9 ]
[ 1469-74-5 ]

Yield	Reaction Conditions	Operation in experiment
	With sulfuric acid; nitric acid 1) 0.5 h, r.t., 2) 1 h, 70 deg C; Yield given. Yields of byproduct given. Title compound not separated from byproducts;

Reference： [1]Onopchenko, Anatoli; Sabourin, Edward T.; Selwitz, Charles M. [Journal of Organic Chemistry, 1981, vol. 46, # 24, p. 5014 - 5017]

14
[ 7020-80-6 ]
[ 21222-05-9 ]
[ 120553-13-1 ]

Yield	Reaction Conditions	Operation in experiment
	Yield given. Multistep reaction;

Reference： [1]Guthrie; Kaplan; Mennona; Tilley; Kierstead; Mullin; LeMahieu; Zawoiski; O'Donnell; Crowley; Yaremko; Welton [Journal of Medicinal Chemistry, 1989, vol. 32, # 8, p. 1820 - 1835]

15
[ 2243-80-3 ]
[ 21222-05-9 ]
[ 60191-42-6 ]
[ 1469-74-5 ]

Yield	Reaction Conditions	Operation in experiment
	With oxygen; Nitrogen dioxide; ozone In dichloromethane at -10℃; for 3h; Yield given. Yields of byproduct given;

Reference： [1]Suzuki, Hitomi; Murashima, Takashi [Journal of the Chemical Society. Perkin transactions I, 1994, # 7, p. 903 - 908]

16
[ 21222-05-9 ]
[ 16965-75-6 ]
[ 86457-78-5 ]

Yield	Reaction Conditions	Operation in experiment
	With tert.-butyl lithium 1.) THF/pentane, -78 deg C, 30 min; 2.) THF, reflux; Yield given. Multistep reaction;

Reference： [1]Crenshaw, Michael D.; Zimmer, Hans [Journal of Organic Chemistry, 1983, vol. 48, # 16, p. 2782 - 2784]

17
[ 21222-05-9 ]
[ 1779-49-3 ]
[ 13005-30-6 ]

Yield	Reaction Conditions	Operation in experiment
	With n-butyllithium 1.) THF, hexane, 3 h, 2.) THF, hexane, reflux, 18 h; Yield given. Multistep reaction;

Reference： [1]Ling, Chris; Minato, Masaki; Lahti, Paul M.; Van Willigen, Hans [Journal of the American Chemical Society, 1992, vol. 114, # 25, p. 9959 - 9969]

18
[ 21222-05-9 ]
[ 1937-19-5 ]
[ 146470-20-4 ]

Yield	Reaction Conditions	Operation in experiment
74%	With hydrogenchloride In ethanol; water for 10h; Heating;

Reference： [1]Richter; Kasbohm; Besch; Hagen [Pharmazie, 1992, vol. 47, # 10, p. 758 - 764]

19
[ 201230-82-2 ]
[ 2865-17-0 ]
[ 21222-05-9 ]

Yield	Reaction Conditions	Operation in experiment
38%	With lithium chloride In tetrahydrofuran at 70℃; for 24h;

Reference： [1]Larock, Richard C.; Hershberger, Susan S. [Journal of Organic Chemistry, 1980, vol. 45, # 19, p. 3840 - 3846]

20
[ 21222-05-9 ]
[ 542-92-7 ]
[ 6602-73-9 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium ethanolate

Reference： [1]Mohrbacher,R.J. et al. [Journal of Organic Chemistry, 1966, vol. 31, p. 2149 - 2159]

21
[ 67-56-1 ]
[ 201230-82-2 ]
[ 13331-27-6 ]
[ 21222-05-9 ]
[ 958-96-3 ]

Yield	Reaction Conditions	Operation in experiment
1: 7% 2: 22%	With tetrakis(triphenylphosphine) palladium⁽⁰⁾ at 25℃; for 20h;

Reference： [1]Cho, Chan Sik; Ohe, Toshiyuki; Uemura, Sakae [Journal of Organometallic Chemistry, 1995, vol. 496, # 2, p. 221 - 226]

22
[ 13331-27-6 ]
[ 21222-05-9 ]
[ 958-96-3 ]

Yield	Reaction Conditions	Operation in experiment
1: 22% 2: 7%	With methanol; tetrakis(triphenylphosphine) palladium⁽⁰⁾; carbon monoxide at 25℃; for 20h;

Reference： [1]Cho, Chan Sik; Ohe, Toshiyuki; Uemura, Sakae [Journal of Organometallic Chemistry, 1995, vol. 496, # 2, p. 221 - 226]

23
[ 167284-99-3 ]
[ 21222-05-9 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium nitrite In N,N-dimethyl-formamide at 100℃; for 3h;
	With sodium nitrite In N,N-dimethyl-formamide at 100℃; for 3h; other 2,2-diaryl-1,1,1-trichloethanes; var. solvents and temp.;
	Multi-step reaction with 2 steps 1: methanol. KOH 2: CrO₃; acetic acid

Reference： [1]Sibrikov, S. G.; Kazin, V. N.; Kopeikin, V. V. [Russian Journal of Organic Chemistry, 1994, vol. 30, # 7.2, p. 1139 - 1140][Zhurnal Organicheskoi Khimii, 1994, vol. 30, # 7, p. 1080]
[2]Sibrikov, S. G.; Kazin, V. N.; Kopeikin, V. V. [Russian Journal of Organic Chemistry, 1994, vol. 30, # 7.2, p. 1139 - 1140][Zhurnal Organicheskoi Khimii, 1994, vol. 30, # 7, p. 1080]
[3]Haskelberg; Lavie [Journal of Organic Chemistry, 1949, vol. 14, p. 498,500]

24
[ 21222-05-9 ]
[ 186968-62-7 ]
[ 86457-78-5 ]

Yield	Reaction Conditions	Operation in experiment
95%	With sodium hydride In tetrahydrofuran for 20h; Heating;

Reference： [1]Muthiah; Kumar, K. Praveen; Kumaraswamy, Sudha; Kumara Swamy [Tetrahedron, 1998, vol. 54, # 47, p. 14315 - 14326]

25
[ 21222-05-9 ]
[ 188840-56-4 ]
C₂₁H₁₅ClN₂O₅ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
96%	With sodium hydride In tetrahydrofuran for 20h; Heating;

Reference： [1]Muthiah; Kumar, K. Praveen; Kumaraswamy, Sudha; Kumara Swamy [Tetrahedron, 1998, vol. 54, # 47, p. 14315 - 14326]

26
[ 40490-41-3 ]
[ 21222-05-9 ]

Yield	Reaction Conditions	Operation in experiment
	With dihydrogen peroxide In water; acetonitrile at 22.5℃;

Reference： [1]Huang, Ruili; Espenson, James H. [Journal of Organic Chemistry, 1999, vol. 64, # 17, p. 6374 - 6376]

27
[ 21222-05-9 ]
[ 57-14-7 ]
3,3'-dinitrobenzophenone N,N-dimethylhydrazone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With trifluoroacetic acid In benzene Heating;

Reference： [1]Stankovic, Sasa; Espenson, James H. [Journal of Organic Chemistry, 2000, vol. 65, # 7, p. 2218 - 2221]

28
3,3'-dinitrobenzophenone N,N-dimethylhydrazone [ No CAS ]
[ 21222-05-9 ]

Yield	Reaction Conditions	Operation in experiment
	With pyridine; dihydrogen peroxide; methyltrioxorhenium(VII) In acetic acid; acetonitrile at 25℃;

Reference： [1]Stankovic, Sasa; Espenson, James H. [Journal of Organic Chemistry, 2000, vol. 65, # 7, p. 2218 - 2221]

29
[ 119-61-9 ]
[ 21222-05-9 ]
[ 1469-74-5 ]
[ 121-92-6 ]
[ 62-23-7 ]

Yield	Reaction Conditions	Operation in experiment
	at 90 - 95℃;

Reference： [1]Bennett; Grove [Journal of the Chemical Society, 1945, p. 378]

30
[ 119-61-9 ]
[ 7664-93-9 ]
[ 21222-05-9 ]
[ 1469-74-5 ]
[ 121-92-6 ]
[ 62-23-7 ]

Yield	Reaction Conditions	Operation in experiment
	at 90℃;

Reference： [1]Bennett; Grove [Journal of the Chemical Society, 1945, p. 378]

31
[ 119-61-9 ]
[ 21222-05-9 ]

Yield	Reaction Conditions	Operation in experiment
	With nitric acid

Reference： [1]Staedel [Justus Liebigs Annalen der Chemie, 1878, vol. 194, p. 347,369][Justus Liebigs Annalen der Chemie, 1883, vol. 218, p. 344]

32
[ 2243-80-3 ]
[ 21222-05-9 ]

Yield	Reaction Conditions	Operation in experiment
	With nitric acid

Reference： [1]Staedel [Chemische Berichte, 1894, vol. 27, p. 2110][Justus Liebigs Annalen der Chemie, 1894, vol. 283, p. 160]

33
[ 21222-05-9 ]
[ 7664-93-9 ]
[ 7697-37-2 ]
3-hydroxy-2,5,3'-trinitro-benzophenone [ No CAS ]
[ 121-92-6 ]

Yield	Reaction Conditions	Operation in experiment
	at 75 - 80℃;

Reference： [1]Bennett; Grove [Journal of the Chemical Society, 1945, p. 378]

34
[ 201230-82-2 ]
bis(3-nitrophenyl)iodonium tetrafluoroborate [ No CAS ]
[ 21222-05-9 ]

Yield	Reaction Conditions	Operation in experiment
44%	With palladium diacetate; indium In N,N-dimethyl-formamide at 20℃; for 1h;

Reference： [1]Zhou, Tao; Chen, Zhen-Chu [Synthetic Communications, 2002, vol. 32, # 22, p. 3431 - 3435]

35
[ 21222-05-9 ]
1-phenylprop-2-en-1-amine hydrochloride [ No CAS ]
[bis-(3-nitro-phenyl)-methylene]-(1-phenyl-allyl)-amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
96%	With titanium tetrachloride; triethylamine In 1,2-dimethoxyethane at -78 - 20℃;

Reference： [1]Oh, Joon Seok; Park, Doh Yeon; Song, Bu Sop; Bae, Jae Gwang; Yoon, Seung Woong; Kim, Young Gyu [Tetrahedron Letters, 2002, vol. 43, # 40, p. 7209 - 7212]

36
[ 616-42-2 ]
[ 21222-05-9 ]
[ 116545-05-2 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride In methanol for 4h; Heating;

Reference： [1]Şişu, Eugen; Şişu, Ioana; Dincǎ, Nicolae; Csunderlik, Carol; Oprean, Ioan; Rusu, Vasile; Mracec, Mircea [Revue Roumaine de Chimie, 2002, vol. 47, # 3-4, p. 339 - 342]

37
[ 21222-05-9 ]
[ 611-80-3 ]

Yield	Reaction Conditions	Operation in experiment
33%	Stage #1: 3,3'-dinitrobenzophenone With hydrogenchloride; tin(ll) chloride at 70℃; for 6h; Stage #2: With hydrogenchloride; sodium nitrite In water at 0℃; for 1h; Stage #3: With sulfuric acid; water Heating;

Reference： [1]Hejaz, Hatem A. M.; Woo, L. W. Lawrence; Purohit, Atul; Reed, Michael J.; Potter, Barry V. L. [Bioorganic and Medicinal Chemistry, 2004, vol. 12, # 10, p. 2759 - 2772]

38
[ 21222-05-9 ]
bis(3-bromo-5-nitrophenyl)methanone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
81%	With N-Bromosuccinimide; sulfuric acid at 60℃; for 2h;

Reference： [1]Rajesh; Somasundaram; Saiganesh; Balasubramanian [Journal of Organic Chemistry, 2007, vol. 72, # 15, p. 5867 - 5869]

39
[ 21222-05-9 ]
sulfamic acid 3-(3-hydroxy-benzoyl)-phenyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: SnCl₂; hydrochloric acid / 6 h / 70 °C 1.2: sodium nitrite; hydrochloric acid / H₂O / 1 h / 0 °C 1.3: 33 percent / sulfuric acid; water / Heating 2.1: 12 percent / sodium hydride; sulfamoyl chloride / dimethylformamide; toluene / 0 - 20 °C

Reference： [1]Hejaz, Hatem A. M.; Woo, L. W. Lawrence; Purohit, Atul; Reed, Michael J.; Potter, Barry V. L. [Bioorganic and Medicinal Chemistry, 2004, vol. 12, # 10, p. 2759 - 2772]

40
[ 21222-05-9 ]
3,3'-benzophenone-O,O'-disufamate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: SnCl₂; hydrochloric acid / 6 h / 70 °C 1.2: sodium nitrite; hydrochloric acid / H₂O / 1 h / 0 °C 1.3: 33 percent / sulfuric acid; water / Heating 2.1: 18 percent / sodium hydride; sulfamoyl chloride / dimethylformamide; toluene / 0 - 20 °C

Reference： [1]Hejaz, Hatem A. M.; Woo, L. W. Lawrence; Purohit, Atul; Reed, Michael J.; Potter, Barry V. L. [Bioorganic and Medicinal Chemistry, 2004, vol. 12, # 10, p. 2759 - 2772]

41
[ 21222-05-9 ]
Acetic acid (1R,2R)-1-acetoxymethyl-2-[bis-(3-nitro-phenyl)-methylene]-amino}-2-phenyl-ethyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: 96 percent / TiCl₄; Et₃N / 1,2-dimethoxy-ethane / -78 - 20 °C 2.1: NMO / OsO₄ / tetrahydrofuran 2.2: Et₃N

Reference： [1]Oh, Joon Seok; Park, Doh Yeon; Song, Bu Sop; Bae, Jae Gwang; Yoon, Seung Woong; Kim, Young Gyu [Tetrahedron Letters, 2002, vol. 43, # 40, p. 7209 - 7212]

42
[ 21222-05-9 ]
Acetic acid (1S,2R)-1-acetoxymethyl-2-[bis-(3-nitro-phenyl)-methylene]-amino}-2-phenyl-ethyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: 96 percent / TiCl₄; Et₃N / 1,2-dimethoxy-ethane / -78 - 20 °C 2.1: NMO / OsO₄ / tetrahydrofuran 2.2: Et₃N

Reference： [1]Oh, Joon Seok; Park, Doh Yeon; Song, Bu Sop; Bae, Jae Gwang; Yoon, Seung Woong; Kim, Young Gyu [Tetrahedron Letters, 2002, vol. 43, # 40, p. 7209 - 7212]

43
[ 21222-05-9 ]
(S)-2-[3-(4-Hydroxy-phenyl)-propionylamino]-4-methyl-pentanoic acid {3-[hydroxy-(3-{(S)-2-[3-(4-hydroxy-phenyl)-propionylamino]-4-methyl-pentanoylamino}-phenyl)-methyl]-phenyl}-amide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 88 percent / NaBH₄ / methanol / 1 h

Reference： [1]Subra, Gilles; Amblard, Muriel; Martinez, Jean [Tetrahedron Letters, 2002, vol. 43, # 50, p. 9221 - 9223]

44
[ 21222-05-9 ]
(S)-2-(3,3-Diphenyl-propionylamino)-4-methyl-pentanoic acid [3-({3-[(S)-2-(3,3-diphenyl-propionylamino)-4-methyl-pentanoylamino]-phenyl}-hydroxy-methyl)-phenyl]-amide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 88 percent / NaBH₄ / methanol / 1 h

Reference： [1]Subra, Gilles; Amblard, Muriel; Martinez, Jean [Tetrahedron Letters, 2002, vol. 43, # 50, p. 9221 - 9223]

45
[ 21222-05-9 ]
[1-[3-({3-[2-benzyloxycarbonylamino-3-(1<i>H</i>-indol-3-yl)-propionylamino]-phenyl}-hydroxy-methyl)-phenylcarbamoyl]-2-(1<i>H</i>-indol-3-yl)-ethyl]-carbamic acid benzyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 88 percent / NaBH₄ / methanol / 1 h

Reference： [1]Subra, Gilles; Amblard, Muriel; Martinez, Jean [Tetrahedron Letters, 2002, vol. 43, # 50, p. 9221 - 9223]

46
[ 21222-05-9 ]
[ 122214-03-3 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 2: 2.) NaOH / 1.) CH₂Cl₂, room temperature, 3 d, 2.) MeOH, H₂O, reflux, 30 min

Reference： [1]Guthrie; Kaplan; Mennona; Tilley; Kierstead; Mullin; LeMahieu; Zawoiski; O'Donnell; Crowley; Yaremko; Welton [Journal of Medicinal Chemistry, 1989, vol. 32, # 8, p. 1820 - 1835]

47
[ 21222-05-9 ]
(E)-5,5-bis(3-nitrophenyl)-N-[4-(3-pyridinyl)butyl)-2,4-pentadienamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 2: 2.) NaOH / 1.) CH₂Cl₂, room temperature, 3 d, 2.) MeOH, H₂O, reflux, 30 min 3: 92 percent / DCC / CH₂Cl₂ / 1.) 0-5 deg C, 60 min, 2.) room temperature, overnight 4: 84 percent / tetrahydrofuran / 1.) room temperature, overnight, 2.) reflux, 3 h

Reference： [1]Guthrie; Kaplan; Mennona; Tilley; Kierstead; Mullin; LeMahieu; Zawoiski; O'Donnell; Crowley; Yaremko; Welton [Journal of Medicinal Chemistry, 1989, vol. 32, # 8, p. 1820 - 1835]

48
[ 21222-05-9 ]
[ 120553-44-8 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 2: 2.) NaOH / 1.) CH₂Cl₂, room temperature, 3 d, 2.) MeOH, H₂O, reflux, 30 min 3: 92 percent / DCC / CH₂Cl₂ / 1.) 0-5 deg C, 60 min, 2.) room temperature, overnight

Reference： [1]Guthrie; Kaplan; Mennona; Tilley; Kierstead; Mullin; LeMahieu; Zawoiski; O'Donnell; Crowley; Yaremko; Welton [Journal of Medicinal Chemistry, 1989, vol. 32, # 8, p. 1820 - 1835]

49
[ 21222-05-9 ]
[ 146028-47-9 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: p-methoxyphenylthionophosphine sulfide - dimer / toluene / 110 °C 2: 75 percent / 20 °C 3: 85 percent / triphenylphosphine / tetrahydrofuran / 16 h / 80 °C 4: 80 percent / Fe, glacial acetic acid / ethanol / 3 h / Heating