[ CAS No. 471-47-6 ] {[proInfo.proName]}

Name: 471-47-6|2-Amino-2-oxoacetic acid|95%
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Quality Control of [ 471-47-6 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 471-47-6 ]

Product Details of [ 471-47-6 ]

CAS No. :	471-47-6	MDL No. :	MFCD00008006
Formula :	C₂H₃NO₃	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	SOWBFZRMHSNYGE-UHFFFAOYSA-N
M.W :	89.05	Pubchem ID :	974
Synonyms :

Calculated chemistry of [ 471-47-6 ]

Physicochemical Properties

Num. heavy atoms :	6
Num. arom. heavy atoms :	0
Fraction Csp3 :	0.0
Num. rotatable bonds :	1
Num. H-bond acceptors :	3.0
Num. H-bond donors :	2.0
Molar Refractivity :	16.41
TPSA :	80.39 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	No
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-7.48 cm/s

Lipophilicity

Log Po/w (iLOGP) :	-0.29
Log Po/w (XLOGP3) :	-0.9
Log Po/w (WLOGP) :	-1.44
Log Po/w (MLOGP) :	-1.92
Log Po/w (SILICOS-IT) :	-1.21
Consensus Log Po/w :	-1.15

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	2.0
Bioavailability Score :	0.56

Water Solubility

Log S (ESOL) :	0.24
Solubility :	155.0 mg/ml ; 1.74 mol/l
Class :	Highly soluble
Log S (Ali) :	-0.31
Solubility :	44.1 mg/ml ; 0.495 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	1.26
Solubility :	1610.0 mg/ml ; 18.0 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.0

Safety of [ 471-47-6 ]

Signal Word:	Danger	Class:	9
Precautionary Statements:	P260-P264-P273-P301+P312-P305+P351+P338-P314	UN#:	3077
Hazard Statements:	H302-H319-H372-H410	Packing Group:	Ⅲ
GHS Pictogram:

Application In Synthesis of [ 471-47-6 ]

* 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 [ 471-47-6 ]

[ 471-47-6 ] Synthesis Path-Downstream 1~88

1
[ 849585-22-4 ]
[ 471-47-6 ]

Reference： [1]Hoppe-Seyler's Zeitschrift fur Physiologische Chemie,1898,vol. 25,p. 325

2
[ 10329-48-3 ]
[ 471-47-6 ]
[ 144-62-7 ]

Reference： [1]Gazzetta Chimica Italiana,1902,vol. 32 I,p. 209

3
[ 617-48-1 ]
[ 471-47-6 ]

Reference： [1]Hoppe-Seyler's Zeitschrift fur Physiologische Chemie,1898,vol. 25,p. 325

4
[ 471-46-5 ]
[ 471-47-6 ]

Reference： [1]Justus Liebigs Annalen der Chemie,1861,vol. 120,p. 237

5
[ 471-47-6 ]
[ 49715-78-8 ]

Reference： [1]Journal of the Chemical Society,1907,vol. 91,p. 177

6
[ 471-47-6 ]
[ 420-05-3 ]

Reference： [1]Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences,1921,vol. 172,p. 160
[2]Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences,1921,vol. 172,p. 160
[3]Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences,1921,vol. 172,p. 160
[4]Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences,1921,vol. 172,p. 160

7
[ 471-47-6 ]
[ 298-12-4 ]

Reference： [1]Patent: DE163842,1905,

8
[ 5972-73-6 ]
[ 64-18-6 ]
[ 471-47-6 ]

Reference： [1]Annales de Chimie (Cachan, France),1842,vol. <3> 4,p. 102
Justus Liebigs Annalen der Chemie,1842,vol. 42,p. 204

9
[ 41886-31-1 ]
[ 64-19-7 ]
[ 74-90-8 ]
[ 471-47-6 ]

Reference： [1]Chemische Berichte,1888,vol. 21,p. 3003
[2]Chemische Berichte,1888,vol. 21,p. 3003

10
[ 617-36-7 ]
[ 57-13-6 ]
[ 471-47-6 ]

Reference： [1]Journal fur praktische Chemie (Leipzig 1954),1874,vol. <2> 9,p. 143

11
[ 471-47-6 ]
[ 95-54-5 ]
[ 15804-19-0 ]

Reference： [1]Journal of the Chemical Society,1955,p. 1079

12
[ 95-92-1 ]
[ 471-47-6 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride; triethanolamine; In ethanol; water;	EXAMPLE 19 Synthesis of silicone resin modified with oxamic acid using an apparatus similar to that used for example 9, into a flask placed with 73 g (0.5 moles) of diethyl oxalate was added dropwise during 1.5 hours an ethanol solution of 380 g of silicone oil (KF 864 made from Sinetsu Silicone Co., LTD.) maintaining reaction temperature at 30 C. and then, the reaction mixture was stirred for 1 hour at 25 C. to get a resin modified with an oxamic acid ester. To this ester was added 30 ml of water and dropped 10.2 g (0.1 mol) of TEA during 30 minutes to carry out a hydrolysis reaction. The aqueous solution thus-obtained was treated with 8.3 ml of concentrated hydrochloric acid getting a wanted silicone resin modified with oxamic acid. Identification was carried out in the same way as described in example 9. The acid value was 10.

Reference： [1]Justus Liebigs Annalen der Chemie,1866,vol. 137,p. 105
[2]Journal of the Chemical Society,1902,vol. 81,p. 1329
[3]Patent: US5663262,1997,A

13
[ 120-89-8 ]
[ 471-46-5 ]
[ 471-47-6 ]
[ 57-13-6 ]

Reference： [1]Angewandte Chemie,1980,vol. 92,p. 858 - 859

14
[ 73278-98-5 ]
[ 471-47-6 ]
N-<3-(3-Piperidinomethyl-phenoxy)propyl>oxamid [ No CAS ]

Reference： [1]Archiv der Pharmazie,1986,vol. 319,p. 434 - 443

15
[ 471-47-6 ]
[ 90-76-6 ]
2-deoxy-2-oxamoylamino-D-mannose [ No CAS ]

Reference： [1]Tetrahedron Letters,1990,vol. 31,p. 225 - 226

16
[ 471-47-6 ]
[ 4710-95-6 ]
2-deoxy-2-oxamoylamino-D-mannose [ No CAS ]

Reference： [1]Chemical and Pharmaceutical Bulletin,1991,vol. 39,p. 1392 - 1396

17
[ 471-47-6 ]
[ 52605-49-9 ]
[ 96082-27-8 ]

Reference： [1]Tetrahedron,1984,vol. 40,p. 5143 - 5152

18
[ 471-47-6 ]
[ 21141-31-1 ]

Reference： [1]Journal of Molecular Structure,1980,vol. 63,p. 13 - 24

19
oxalic anhydride [ No CAS ]
[ 471-47-6 ]

Reference： [1]Journal of the American Chemical Society,1984,vol. 106,p. 4814 - 4818

20
N-hexyloxalamidine [ No CAS ]
[ 471-47-6 ]
[ 142-81-4 ]
N-Hexyl-oxalamic acid [ No CAS ]

Reference： [1]Bioorganic Chemistry,1995,vol. 23,p. 217 - 226

21
[ 56-40-6 ]
[ 64-18-6 ]
[ 471-47-6 ]
[ 144-62-7 ]

Reference： [1]Water Research,1999,vol. 33,p. 433 - 441

22
[ 19406-51-0 ]
[ 60939-21-1 ]
[ 471-47-6 ]
[ 127-17-3 ]
[ 298-12-4 ]

Reference： [1]Environmental science and technology,2000,vol. 34,p. 497 - 504

23
[ 56-40-6 ]
aqueous potassium permanganate [ No CAS ]
[ 471-47-6 ]
[ 124-38-9 ]
[ 144-62-7 ]

Reference： [1]Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences,1874,vol. 79,p. 808
Jahresbericht ueber die Fortschritte der Chemie und Verwandter Theile Anderer Wissenschaften,1874,p. 847

24
[ 7664-41-7 ]
[ 56-40-6 ]
potassium permanganate [ No CAS ]
ammonium sulfate [ No CAS ]
[ 471-47-6 ]
[ 77287-34-4 ]

Reference： [1]Hoppe-Seyler's Zeitschrift fur Physiologische Chemie,1898,vol. 25,p. 325

32
[ 471-47-6 ]
[ 10026-13-8 ]
[ 10025-87-3 ]
[ 49715-78-8 ]

Reference： [1]Chemische Berichte,1886,vol. 19,p. 3229

33
[ 471-47-6 ]
[ 7664-41-7 ]
potassium permanganate [ No CAS ]
[ 420-05-3 ]

Reference： [1]Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences,1921,vol. 172,p. 160

Yield	Reaction Conditions	Operation in experiment
		Further examples are ... p-carboxyanilide, p-methoxycarbonylanilide, o-carboxyanilide and o-hydroxyanilide. carboxymethylamide, carboxyethylamide, carboxypropylamide, and carboxybutylamide. ...

35
[ 875226-16-7 ]
[ 7732-18-5 ]
[ 471-47-6 ]

Reference： [1]Journal fur praktische Chemie (Leipzig 1954),1915,vol. <2>91,p. 434

36
acidic ammonium oxalate [ No CAS ]
[ 471-47-6 ]

Reference： [1]Annales de Chimie (Cachan, France),1842,vol. <3> 4,p. 102
Justus Liebigs Annalen der Chemie,1842,vol. 42,p. 204

37
amino acid [ No CAS ]
[ 471-47-6 ]

Reference： [1]Hoppe-Seyler's Zeitschrift fur Physiologische Chemie,1898,vol. 25,p. 325

38
[ 10329-48-3 ]
bromine water [ No CAS ]
[ 471-47-6 ]

Reference： [1]Gazzetta Chimica Italiana,1926,vol. 56,p. 758
Gazzetta Chimica Italiana,1932,vol. 62,p. 1053

39
oxalamidehydroxamic acid [ No CAS ]
[ 471-47-6 ]

Reference： [1]Gazzetta Chimica Italiana,1926,vol. 56,p. 758
Gazzetta Chimica Italiana,1932,vol. 62,p. 1053

40
oxamethane [ No CAS ]
[ 471-47-6 ]

Reference： [1]Chemische Berichte,1889,vol. 22,p. 1569

41
protein [ No CAS ]
[ 471-47-6 ]

Reference： [1]Hoppe-Seyler's Zeitschrift fur Physiologische Chemie,1898,vol. 25,p. 325

42
[ 5447-64-3 ]
[ 7664-41-7 ]
[ 563-83-7 ]
[ 471-47-6 ]

Reference： [1]Chemische Berichte,1898,vol. 31,p. 197

43
glue [ No CAS ]
[ 471-46-5 ]
[ 471-47-6 ]

Reference： [1]Chemiker-Zeitung, Chemische Apparatur,1905,vol. 29,p. 604

44
[ 471-47-6 ]
[ 7732-18-5 ]
alkalies [ No CAS ]
+or* acids [ No CAS ]
[ 144-62-7 ]

Reference： [1]Justus Liebigs Annalen der Chemie,1861,vol. 120,p. 237

45
[ 471-47-6 ]
[ 7664-41-7 ]
potassium permanganate [ No CAS ]
ammonium sulfate [ No CAS ]
[ 57-13-6 ]

Reference： [1],1896,vol. 37,p. 426
Chemisches Zentralblatt,1896,vol. 67,p. 389

46
[ 617-49-2 ]
[ 7664-41-7 ]
[ 471-47-6 ]
[ 144-62-7 ]
[ 57-13-6 ]

Reference： [1]Chemische Berichte,1905,vol. 38,p. 459

47
3-acetoxy-4-oxo-2,5-diphenyl-hex-2-enedinitrile [ No CAS ]
ammonium hydroxide [ No CAS ]
[ 471-47-6 ]
[ 144-62-7 ]
[ 140-29-4 ]
[ 103-81-1 ]

Reference： [1]Justus Liebigs Annalen der Chemie,1894,vol. 282,p. 66,81

48
[ 471-47-6 ]
[ 34036-16-3 ]
[ 19501-58-7 ]
4-(ethoxycarbonyl)-5-isobutyl-1-(4-methoxyphenyl)-1H-pyrazole-3-carboxylic acid [ No CAS ]

Reference： [1]European Journal of Organic Chemistry,2005,p. 4621 - 4627

49
[ 471-47-6 ]
[ 34036-16-3 ]
[ 1073-70-7 ]
1-(4-chlorophenyl)-4-(ethoxycarbonyl)-5-isobutyl-1H-pyrazole-3-carboxylic acid [ No CAS ]

Reference： [1]European Journal of Organic Chemistry,2005,p. 4621 - 4627

50
[ 471-47-6 ]
[ 149819-14-7 ]
[ 128741-75-3 ]

Yield	Reaction Conditions	Operation in experiment
70%	With 1,1'-carbonyldiimidazole; In N,N-dimethyl-formamide; at 20℃;Inert atmosphere;	Intermediate 11 (0.20 g, 0.76 mmol) was dissolved in 2 mL of N,N-dimethylformamide (DMF) then <strong>[471-47-6]oxamic acid</strong> (<strong>[471-47-6]oxamic acid</strong>, 0.10 g, 1.14 mmol) was added in sequence. And carbonyl diimidazole (CDI, 0.20 g, 1.23 mmol), The system was then argon protected and stirred at room temperature overnight. After TLC, the reaction was completed, and 1 ml of water was added to continue stirring for 30 min. After removing the solvent under reduced pressure, The residue was purified on silica gel to give 177 mg of white solid, intermediate 12, yield 70%

Reference： [1]Journal of Organic Chemistry,2005,vol. 70,p. 9892 - 9904
[2]Patent: CN110256422,2019,A .Location in patent: Paragraph 0083-0086

51
[ 471-47-6 ]
[ 19501-58-7 ]
[ 94-02-0 ]
4-(ethoxycarbonyl)-1-(4-methoxyphenyl)-5-phenyl-1H-pyrazole-3-carboxylic acid [ No CAS ]

Reference： [1]European Journal of Organic Chemistry,2005,p. 4621 - 4627

52
[ 471-47-6 ]
[ 1073-70-7 ]
[ 94-02-0 ]
1-(4-chlorophenyl)-4-(ethoxycarbonyl)-5-phenyl-1H-pyrazole-3-carboxylic acid [ No CAS ]

Reference： [1]European Journal of Organic Chemistry,2005,p. 4621 - 4627

53
[ 471-47-6 ]
[ 7400-27-3 ]
[ 94-02-0 ]
1-tert-butyl-4-(ethoxycarbonyl)-5-phenyl-1H-pyrazole-3-carboxylic acid [ No CAS ]

Reference： [1]European Journal of Organic Chemistry,2005,p. 4621 - 4627

54
[ 471-47-6 ]
[ 94-02-0 ]
[ 100-63-0 ]
[ 872988-43-7 ]

Reference： [1]European Journal of Organic Chemistry,2005,p. 4621 - 4627

55
[ 471-47-6 ]
[ 94-02-0 ]
[ 60-34-4 ]
4-(ethoxycarbonyl)-1-methyl-5-phenyl-1H-pyrazole-3-carboxylic acid [ No CAS ]

Reference： [1]European Journal of Organic Chemistry,2005,p. 4621 - 4627

56
[ 471-47-6 ]
[ 19501-58-7 ]
[ 105-45-3 ]
4-(methoxycarbonyl)-1-(4-methoxyphenyl)-5-methyl-1H-pyrazole-3-carboxylic acid [ No CAS ]

Reference： [1]European Journal of Organic Chemistry,2005,p. 4621 - 4627

57
[ 471-47-6 ]
[ 1073-70-7 ]
[ 105-45-3 ]
[ 268544-89-4 ]

Reference： [1]European Journal of Organic Chemistry,2005,p. 4621 - 4627

58
[ 471-47-6 ]
[ 7400-27-3 ]
[ 105-45-3 ]
[ 268544-88-3 ]

Reference： [1]European Journal of Organic Chemistry,2005,p. 4621 - 4627

59
[ 471-47-6 ]
[ 105-45-3 ]
[ 100-63-0 ]
[ 198135-47-6 ]

Reference： [1]European Journal of Organic Chemistry,2005,p. 4621 - 4627

60
[ 471-47-6 ]
[ 105-45-3 ]
[ 60-34-4 ]
[ 268544-87-2 ]

Reference： [1]European Journal of Organic Chemistry,2005,p. 4621 - 4627

61
[ 471-47-6 ]
[ 34036-16-3 ]
[ 100-63-0 ]
4-(ethoxycarbonyl)-5-isobutyl-1-phenyl-1H-pyrazole-3-carboxylic acid [ No CAS ]

Reference： [1]European Journal of Organic Chemistry,2005,p. 4621 - 4627

62
[ 471-47-6 ]
[ 34036-16-3 ]
[ 60-34-4 ]
4-(ethoxycarbonyl)-5-isobutyl-1-methyl-1H-pyrazole-3-carboxylic acid [ No CAS ]

Reference： [1]European Journal of Organic Chemistry,2005,p. 4621 - 4627

63
N-[acetyl-1-14-C]-S-(1,2,3,4,4-pentachloro-1,3-butadienyl)-L-cysteine [ No CAS ]
[ 471-47-6 ]
S-(1,2,3,4,4-pentachlorobutadienyl)-L-cysteine [ No CAS ]

Reference： [1]Toxicology Letters,2003,vol. 138,p. 63 - 73
[2]Toxicology Letters,2003,vol. 138,p. 63 - 73

64
[ 503598-78-5 ]
[ 471-47-6 ]
N-(3-carbamoyl-3,3-diphenylpropyl)oxamide [ No CAS ]

Reference： [1]Chemical and Pharmaceutical Bulletin,2007,vol. 55,p. 1039 - 1043

65
[ 471-47-6 ]
(2S,3S,4S,5R)-1-benzyloxy-5-<(benzyloxycarbonyl)amino>-2,3:4,6-bis(isopropylidenedioxy)hexane [ No CAS ]
2-deoxy-1,3:4,5-di-O-isopropylidene-2-oxamoylamino-D-mannitol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
80%	With 1,1'-carbonyldiimidazole; In N,N-dimethyl-formamide; at 25℃;	Example 6 Preparation of 2-deoxy-1,3:4,5-DI-O-isopropylidene-2-oxamoylamino-D-mannitol <strong>[471-47-6]oxamic acid</strong> (1.02 g, 11.5 mmol) was dissolved in 15 ML of anhydrous N,N-dimethylformamide, at 60 C., under an inert atmosphere and the resulting solution cooled to 25 C. In a separate flask, 1,1'-carbonyldiimidazole (CDI) (1.93 g, 11.9 mmol) was dissolved in 15 ML of anhydrous N,N-dimethylformamide, under an inert atmosphere, at 25 C. In another flask, the amino alcohol (5) (2 g, 7.7 mmol) was dissolved in 5 ML of anhydrous N,N-dimethylformamide, under an inert atmosphere, at 25 C. The <strong>[471-47-6]oxamic acid</strong> solution was added dropwise, at 25 C., to the CDI solution over a period of 30 minutes.After stirring for a further 20 minutes at 25 C., the amino alcohol solution was added dropwise over 10 minutes.The reaction mixture was left to stir at 25 C. overnight.Analysis by TLC (9:1, ethyl acetate:methanol) indicated the presence of starting material.A further portion of activated <strong>[471-47-6]oxamic acid</strong> was made from additional solutions of <strong>[471-47-6]oxamic acid</strong> (0.52 g, 5.86 mmol) and CDI (1.0 g, 6.17 mmol) in 5 ML anhydrous N,N-dimethylformamide in an identical fashion to that above.The solution of additional activated <strong>[471-47-6]oxamic acid</strong> is then added dropwise over 15 minutes to the original reaction mixture and stirring continued at 25 C. for 1 hour.Analysis by TLC indicated complete consumption of starting material.water (1 ML) was added to the reaction mixture with continued stirring for 30 minutes.The resulting mixture was then concentrated under reduced pressure and the residue subjected to dry-flash chromatography to provide (6) (2.04 g, 80%) as a white solid. This material has been previously reported (H. Kayakiri, C. Kasahara, K. Nakamura, T. Oku, and M. Hashimoto, Chem. Pharm. Bull., 39, 1392, 1991) and data obtained corresponded to that observed in the literature.

Reference： [1]Patent: US2004/63973,2004,A1 .Location in patent: Page 9-10

66
6-chloro-N₄-(2-chloro-phenyl)-quinoline-3,4-diamine [ No CAS ]
[ 471-47-6 ]
8-chloro-1-(2-chloro-phenyl)-1H-imidazo[4,5-c]quinoline-2-carboxylic acid amide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With PPA; at 125℃; for 5h;	1 g (3.287 mmol) of 6-chloro-N4- (2-chloro-phenyl)-quinoline-3, 4-diamine and 0.6 g (0.73 mmol) <strong>[471-47-6]oxamic acid</strong> in 5 g polyphosphoric acid (83%, Fluka) are heated and kept at 125 C during 5 h. After cooling, 50 ml 25% ammonia solution is added carefully under stirring to the cold reaction medium. The title compound precipitates partially and is filtered off, washed with water and diethyl ether and dried at 60C for 16 h. mp: 194-195C ; MS: 357 (M++1) ; HPLC: trek=8. 96 min (Grad 1). Additional material can be obtained from the inorganic phase by extraction with ethyl acetate and purification by chromatography (ethyl acetate-hexane 4: 1).

Reference： [1]Patent: WO2003/97641,2003,A2 .Location in patent: Page/Page column 79

67
[ 877165-61-2 ]
[ 471-47-6 ]
7-(4-aminooxalyl-piperazin-1-ylmethyl)-1-methyl-1H-indole-2-carboxylic acid (5-tert-butyl-3-methanesulfonylamino-2-methoxy-phenyl)-amide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
87%	With benzotriazol-1-ol; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; In DMF (N,N-dimethyl-formamide); at 20℃; for 72h;	To a solution of 4-[2-(5-tert-butyl-3-methanesulfonylamino-2-methoxy-phenylcarbamoyl)-1-methyl-1H-indol-7-ylmethyl]-piperazine-1-carboxylic acid tert-butyl ester (87 mg, 0.139 mmol) in MeOH (1 mL) was added concentrated HCl (50 muL). The mixture heated to reflux for 2 h, cooled to room temperature and basified with NaHCO3 (sat.) to pH~9. The mixture was then extracted with EtOAc several times. The combined organic extracts were washed with brine, dried over MgSO4 and concentrated to give the desired deprotected piperazine as a white foam (87 mg). The product was characterized by 1H NMR and mass spectroscopy. To a solution of <strong>[471-47-6]oxamic acid</strong> (10.24 mg, 0.115 mmol) in DMF (1 mL) was added HATU (43.7 mg, 0.115 mmol), HOAT (7.83 mg, 0.058 mmol) and diisopropylethylamine (40 mul, 0.230 mmol). After 10 min, the above deprotected piperazine (13 mg, 0.025 mmol) was added. The mixture was stirred at room temperature for 3 days. The reaction mixture was then diluted with EtOAc, washed with NaHCO3 (sat.) and brine in sequence. The organic layer was dried over MgSO4 and concentrated. The crude product was purified by silica gel chromatography to give 13 mg of the title compound as a white foam, yield 87%. ESI MS m/z 599.65 [M+H]+.

Reference： [1]Patent: US2006/46986,2006,A1 .Location in patent: Page/Page column 28

68
[ 471-47-6 ]
ammonium chloride [ No CAS ]
[ 541-41-3 ]
[ 141332-75-4 ]
[ 161918-67-8 ]
[ 471-46-5 ]

Yield	Reaction Conditions	Operation in experiment
30%	With 4-methyl-morpholine; In methanol; 1,2-dimethoxyethane; dichloromethane;	EXAMPLE 15 N-[2-(3-Cyclopentyloxy-4-methoxyphenyl)ethyl]oxamide To a suspension of <strong>[471-47-6]oxamic acid</strong> (1.76 g, 20 mmol) in 1,2-dimethoxyethane (75 mL) under an argon atmosphere was added dropwise N-methylmorpholine (2.55 mL, 23 mmol) followed by ethyl chloroformate (2.20 mL, 23 mmol). After stirring for 1 h at room temperature, a solution of 2-(3-cyclopentyloxy-4-methoxy-phenyl)ethylamine (4.65 g, 20 mmol) in 1,2-dimethoxyethane (30 mL) was added over 5 min, and the resulting mixture was stirred for 2 h. Saturated aqueous ammonium chloride was added and the solvent was removed under reduced pressure. The solid residue was dissolved in methanol/methylene chloride, washed successively with water, 10% hydrochloric acid, aqueous sodium bicarbonate and water and dried (potassium carbonate). The solvent was removed in vacuo and the residue was purified by flash chromatography, eluding with 1% i-propanol/methylene chloride to provide the oxamide (1.82 g, 30%): m.p. 175-175.5 C. Analysis Calc. for C16 H22 N2 O4: C 62.73, H 7.24, N 9.14; found: C 62.61, H 7.32, N 8.98.

Reference： [1]Patent: US5393788,1995,A

69
N-[2-(3,4-dimethoxyphenyl)ethyl]-N-hydroxyamine [ No CAS ]
[ 471-47-6 ]
ammonium chloride [ No CAS ]
[ 541-41-3 ]
[ 471-46-5 ]

Yield	Reaction Conditions	Operation in experiment
17%	With 4-methyl-morpholine; In 1,2-dimethoxyethane;	c) N-[2-(3,4-Dimethoxyphenyl)ethyl]-N-hydroxamide. To a suspension of <strong>[471-47-6]oxamic acid</strong> (195 mg, 2.21 mmol) in 1,2-dimethoxyethane (7 mL) under an argon atmosphere was added dropwise N-methylmorpholine (0.27 mL, 2.42 mmol), followed by ethyl chloroformate (0.23 mL, 2.42 mmol). After stirring for 1 h at room temperature, a solution of N-[2-(3,4-dimethoxyphenyl)ethyl]-N-hydroxyamine (417 mg, 2.10 mmol) in 1,2-dimethoxyethane (5 mL) was added, and the resulting mixture was stirred for 4 h. Saturated aqueous ammonium chloride was added, and the mixture was extracted with methylene chloride (2*). The combined organic extracts were washed successively with 10% hydrochloric acid and water and dried (potassium carbonate). The solvent was removed in vacuo and the residue was purified by flash chromatography, eluding with 5% methanol/methylene chloride, and recrystallized from methanol/methylene chloride to provide the oxamide (98 mg, 17%): m.p. 143-144 C. Analysis Calc. for C12 H16 N2 O5.3/8 H2 O: C 52.41, H 6.14, N 10.19; found: C 52.24, H 5.75, N 10.12.

Reference： [1]Patent: US5393788,1995,A

70
[ 471-47-6 ]
[ 141333-37-1 ]
[ 543-27-1 ]
[ 471-46-5 ]

Yield	Reaction Conditions	Operation in experiment
22%	With 4-methyl-morpholine; In 1,2-dimethoxyethane; chloroform;	To a suspension of <strong>[471-47-6]oxamic acid</strong> (0.27 g, 3 mmol) in 1,2-dimethoxyethane (10 mL) under an argon atmosphere was added dropwise N-methylmorpholine (0.36 mL, 3.3 mmol) followed by isobutyl chloroformate (0.43 mL, 3.3 mmol). After stirring for 1.5 h at room temperature, a solution of 2-(3-cyclopentyloxy-4-methoxyphenyl)propylamine (0.5 g, 2 mmol) in 1,2-dimethoxyethane (5 mL) was added and the resulting mixture was stirred overnight. The solvent was removed under reduced pressure. The solid residue was dissolved in chloroform, washed successively with dilute hydrochloric acid and water and dried (sodium sulfate). The solvent was removed in vacuo and the residue was purified by flash chromatography, eluding with 10% ether/chloroform. A second flash chromatography elution with 50% ethyl acetate/chloroform provided the oxamide (0.14 g, 22%): m.p. 175-176.5 C. Analysis Calc. for C17 H24 N2 O4: C 63.73, H 7.55, N 8.74; found: C 63.80, H 7.69, N 8.65.

Reference： [1]Patent: US5393788,1995,A

71
[ 926029-00-7 ]
[ 471-47-6 ]
2-((+)-(S)-3-{2-[4-(1H-Indol-5-yl)-piperazin-1-yl]-ethyl}-2,3-dihydro-1H-indol-1-yl)-2-oxo-acetamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With 1,1'-carbonyldiimidazole; In N,N-dimethyl-formamide; at 20℃; for 1h;	3a, 2-((+)-(S)-3-{2-[4-(1H-Indol-5-yl)-piperazin-1-yl]-ethyl}2,3-dihydro-1H-indol-1-yl)-2-oxo-acetamide; To a solution of oxalamic acid (2.35 g, 0.026 mol) and 1,1'-carbonyldiimidazole (4.66 g, 0.029 mol) in dry N,N-dimethyl formamide (50 mL) was slowly added a solution of 5-{4-[(S)-2-(2,3-dihydro-1H-indol-3-yl)-ethyl]-piperazin-1-yl}-1H-indole (8.3 g, 0.024 mol) in N,N-dimethyl formamide (75 mL). The resulting mixture was stirred at room temperature for 1 h, filtered and poured onto brine. The aqueous phase was extracted with ethyl acetate, and the combined organic phase was washed with brine, dried (MgSO4), filtered and concentrated in vacuo. The residue was purified by flash chromatography (ethyl acetate/heptane/triethylamine 70:25:5) to give the title compound as an oil (6.5 g). The oil was precipitated from ethyl acetate to give a powder (4.1 g). Assignment of the optical rotation was done in dimethyl sulfoxide. LC/MS (m/z) 418 (MH+); RT=1.62 (Method A).
	With 1,1'-carbonyldiimidazole; In N,N-dimethyl-formamide; at 20℃; for 1h;	To a solution of oxalamic acid (2.35g, 0.026 mol) and l,r-carbonyldiimidazole (4.66 g, 0.029 mol) in dry JV,iV-dimethyl formamide (50 mL) was slowly added a solution of 5-{4- [(5)-2-(2,3-dihydro-lH-indol-3-yl)-ethyl]-piperazin-l-yl}-lH-indole (8.3 g, 0.024 mol) in iV,iV-dimethyl formamide (75 mL). The resulting mixture was stirred at room temperature for 1 h, filtered and poured onto brine. The aqueous phase was extracted with ethyl acetate, and the combined organic phase was washed with brine, dried (MgSO4), filtered and concentrated in vacuo. The residue was purified by flash chromatography (ethyl acetate/heptane/triethylamine 70:25:5) to give the title compound as an oil (6.5 g). The oil was precipitated from ethyl acetate to give a powder (4.1 g). Assignment of the optical rotation was done in dimethyl sulfoxide.LC/MS (m/z) 418 (MH+); RT = 1.62 (Method A).

Reference： [1]Patent: US2007/43058,2007,A1 .Location in patent: Page/Page column 16
[2]Patent: WO2007/19867,2007,A1 .Location in patent: Page/Page column 41-42

72
2-fluoro-3'-([(3R,4S)-3-phenylpiperidin-4-yl]amino}methyl)-4'-(trifluoromethoxy)biphenyl-4-carbonitrile dihydrochloride [ No CAS ]
[ 471-47-6 ]
2-[(3R,4S)-4-([4'-cyano-2'-fluoro-4-(trifluoromethoxy)biphenyl-3-yl]methyl}amino)-3-phenylpiperidin-1-yl]-2-oxoacetamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
61%	With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In N,N-dimethyl-formamide; at 10 - 35℃; for 13h;	Example 104; EPO <DP n="141"/>2- [ ( 3R, 4 S ) -4 - ( { [ 4 ' -cyano-2 ' - f luoro-4 -(trifluoromethoxy) biphenyl-3-yl ] methyl } amino) -3- phenylpiperidin-1-yl] -2-oxoacetamide; To a solution of the compound (380 mg) obtained in Example 94, Et3N (213 mg) and <strong>[471-47-6]oxamic acid</strong> (94 mg) in DMF (6 mL) were added WSC-HCl (201 mg) and HOBt-H2O (161 mg) and the mixture was stirred at room temperature for 13 hr. The reaction mixture was poured into water, and the product was extracted with ethyl acetate. The organic layer was washed with a saturated aqueous sodium hydrogen carbonate solution and brine and dried, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (solvent gradient; 50-»100% ethyl acetate/hexane) to give the title compound (230 mg, 61%) as white crystals.Melting point: 142-1440C Elemental analysis: C28H24F4N4O3Found C, 62.09; H, 4.55; N, 10.27 Calcd. C, 62.22; H, 4.48; N, 10.37 MS(ESI+) : 541 (M+H)

Reference： [1]Patent: WO2007/15588,2007,A1 .Location in patent: Page/Page column 139-140

73
[ 471-47-6 ]
praseodymium⁽³⁺⁾ [ No CAS ]
hexaaquatris(oxalato)dipraseodymium(III) pentahydrate [ No CAS ]

Reference： [1]Acta Crystallographica, Section C: Crystal Structure Communications,1988,vol. 44,p. 174 - 175

74
copper(II) nitrate trihydrate [ No CAS ]
[ 471-47-6 ]
[ 18694-40-1 ]
[ 121865-94-9 ]

Reference： [1]Inorganic Chemistry,1989,vol. 28,p. 3378 - 3386

75
[ 75-13-8 ]
[ 144-62-7 ]
[ 471-47-6 ]

Reference： [1]Gmelin Handbuch der Anorganischen Chemie,Gmelin Handbook: C: MVol.D1, 34.7.4, page 343 - 344
[2]Gmelin Handbuch der Anorganischen Chemie,Gmelin Handbook: C: MVol.D1, 34.7.4, page 343 - 344

76
praseodymium trichloride hydrate [ No CAS ]
[ 471-47-6 ]
Pr⁽³⁺⁾*3(H₂NCOCOO)^(1-)*2H₂O [ No CAS ]

Reference： [1]Journal of the Less-Common Metals,1990,vol. 158,p. 1 - 14

77
europium trichloride hydrate [ No CAS ]
[ 471-47-6 ]
Eu⁽³⁺⁾*3(H₂NCOCOO)^(1-)*3H₂O [ No CAS ]

Reference： [1]Journal of the Less-Common Metals,1990,vol. 158,p. 1 - 14

78
[ 471-47-6 ]
[ 12775-96-1 ]
4K⁽¹⁺⁾*Cu{HNC(O)C(O)O}3^(4-)=K₄Cu{HNC(O)C(O)O}3 [ No CAS ]

Reference： [1]Bulletin des Societes Chimiques Belges,1986,vol. 95,p. 13 - 28

79
lanthanumtrichloridehydrate [ No CAS ]
[ 471-47-6 ]
La⁽³⁺⁾*3(H₂NCOCOO)^(1-)*2H₂O [ No CAS ]

Reference： [1]Journal of the Less-Common Metals,1990,vol. 158,p. 1 - 14

80
ytterbium trichloride hydrate [ No CAS ]
[ 471-47-6 ]
Yb⁽³⁺⁾*3H₂NCOCOO^(1-)*H₂O [ No CAS ]

Reference： [1]Journal of the Less-Common Metals,1990,vol. 158,p. 1 - 14

81
[ 471-47-6 ]
[ 6046-93-1 ]
2K⁽¹⁺⁾*{Cu(C₂HNO₃)2}^(2-)=K₂{Cu(C₂HNO₃)2} [ No CAS ]

Reference： [1]Chemische Berichte,1913,vol. 46,p. 1457 - 1466

82
samarium trichloride hydrate [ No CAS ]
[ 471-47-6 ]
Sm⁽³⁺⁾*3(H₂NCOCOO)^(1-)*3H₂O [ No CAS ]

Reference： [1]Journal of the Less-Common Metals,1990,vol. 158,p. 1 - 14

83
holmium trichloride hydrate [ No CAS ]
[ 471-47-6 ]
Ho⁽³⁺⁾*3(H₂NCOCOO)^(1-)*3H₂O [ No CAS ]

Reference： [1]Journal of the Less-Common Metals,1990,vol. 158,p. 1 - 14

84
cerium trichloride [ No CAS ]
[ 471-47-6 ]
Ce⁽³⁺⁾*3(H₂NCOCOO)^(1-)*2H₂O [ No CAS ]

Reference： [1]Journal of the Less-Common Metals,1990,vol. 158,p. 1 - 14

85
rhodium(III) oxide [ No CAS ]
[ 471-47-6 ]
K₃{Rh(oxamate)3}*H₂O [ No CAS ]

Reference： [1]Monatshefte fur Chemie,1982,vol. 113,p. 155 - 162

86
erbium trichloride hydrate [ No CAS ]
[ 471-47-6 ]
Er⁽³⁺⁾*3(H₂NCOCOO)^(1-)*3H₂O [ No CAS ]

Reference： [1]Journal of the Less-Common Metals,1990,vol. 158,p. 1 - 14

87
gadolinium trichloride hydrate [ No CAS ]
[ 471-47-6 ]
Gd⁽³⁺⁾*3(H₂NCOCOO)^(1-)*2H₂O [ No CAS ]

Reference： [1]Journal of the Less-Common Metals,1990,vol. 158,p. 1 - 14

88
neodymium trichloride hydrate [ No CAS ]
[ 471-47-6 ]
Nd⁽³⁺⁾*3(H₂NCOCOO)^(1-)*2H₂O [ No CAS ]

Reference： [1]Journal of the Less-Common Metals,1990,vol. 158,p. 1 - 14

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[ 471-47-6 ] Synthesis Path-Downstream 1~88

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