58933-52-1|4-((((Benzyloxy)carbonyl)amino)methyl)benzoic acid| Ambeed

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Quality Control of [ 58933-52-1 ] Purity: 95% SDS Specification

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Product Details of [ 58933-52-1 ]

CAS No. :	58933-52-1
Formula :	C₁₆H₁₅NO₄
M.W :	285.30
SMILES Code :	O=C(O)C1=CC=C(CNC(OCC2=CC=CC=C2)=O)C=C1
MDL No. :	MFCD02094410
InChI Key :	QWHYEFZPTSTTSR-UHFFFAOYSA-N
Pubchem ID :	1479997

Safety of [ 58933-52-1 ]

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 [ 58933-52-1 ]

* 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 [ 58933-52-1 ]

[ 58933-52-1 ] Synthesis Path-Downstream 1~41

1
[ 58933-52-1 ]
[ 2386-57-4 ]
[ 82957-06-0 ]
[ 82956-00-1 ]

References: [1]Chemical and Pharmaceutical Bulletin,1985,vol. 33,p. 1458 - 1471.

2
[ 58933-52-1 ]
[ 99-05-8 ]
[ 135321-23-2 ]

References: [1]Journal of Medicinal Chemistry,1992,vol. 35,p. 4393 - 4407.

3
[ 58933-52-1 ]
[ 148145-41-9 ]
((S)-1-{2-[4-(Benzyloxycarbonylamino-methyl)-benzoylamino]-acetyl}-4-tert-butoxycarbonylmethyl-3-oxo-piperazin-2-yl)-acetic acid tert-butyl ester [ No CAS ]

References: [1]Journal of Medicinal Chemistry,1998,vol. 41,p. 489 - 502.

4
[ 58933-52-1 ]
[ 32677-01-3 ]
[ 162877-53-4 ]

References: [1]Chemical and Pharmaceutical Bulletin,1998,vol. 46,p. 255 - 273.

5
[ 54553-19-4 ]
[ 58933-52-1 ]
4-(2-phenoxy-ethoxy)-benzoic acid 1,1,3-trioxo-1,3-dihydro-1λ⁶-benzo[<i>d</i>]isothiazol-2-ylmethyl ester [ No CAS ]

References: [1]Journal of Medicinal Chemistry,1998,vol. 41,p. 4854 - 4860.

6
[ 54553-19-4 ]
[ 58933-52-1 ]
4-(benzyloxycarbonylamino-methyl)-benzoic acid 1,1,3-trioxo-1,3-dihydro-1λ⁶-benzo[<i>d</i>]isothiazol-2-ylmethyl ester [ No CAS ]

References: [1]Journal of Medicinal Chemistry,1998,vol. 41,p. 4854 - 4860.

7
[ 58933-52-1 ]
[ 85916-13-8 ]
[ 851513-73-0 ]

References: [1]Journal of the American Chemical Society,2003,vol. 125,p. 4420 - 4421.
[2]Journal of the American Chemical Society,2004,vol. 126,p. 12833 - 12842.

8
[ 58933-52-1 ]
[ 148930-30-7 ]
C₇₁H₇₀N₂O₁₉ [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry,2003,vol. 11,p. 1851 - 1857.

9
[ 56-91-7 ]
[ 501-53-1 ]
[ 58933-52-1 ]

Yield	Reaction Conditions	Operation in experiment
87%	With sodium hydroxide; In tetrahydrofuran; water; at 0 - 20℃; for 16h;	Benzyl chloroformate (10.3 mL, 72.7 mmol) and 2 M NaOH solution (33 mL, 66 mmol) were simultaneously added dropwise to a stirred solution of 4-aminomethylbenzoic acid (29) (10.0 g, 66.2 mmol) in 2 M NaOH solution (33 mL) and THF (30 mL) at 0 C. The mixture was stirred at 20 C for 16 h, then the organic solvent was evaporated and the residue acidified with 2 M HC1 until the pH of the mixture was 2-3. The precipitate was filtered, washed with water (250 mL), washed with EtOH (50 mL), and finally washed with Et20 (100 mL). The solid was dried under vacuum to give acid 2 (16.43 g, 87%) as a white powder: mp 190-192 C [lit. (Loge et. al., J. Enzyme Inhibit. Med. Chem. 2002, 17, 381-390) mp (toluene) 194-195 C; 1H NMR δ 7.85 (br d, 2 H, H-2, H-6), 7.82 (br t, J = 6.1 Hz, 1 H, NHC02), 7.30-7.40 (m, 5 H, H-2', H-3', H-4', H-5', H-6'), 7.27 (br d, J = 8.2 Hz, 2 H, H-3, H-5), 5.05 (s, 2 H, OCH2), 4.24 (d, J = 6.1 Hz, 2 H, CH2N).
87%	With sodium hydroxide; In tetrahydrofuran; at 0 - 20℃; for 16h;	Benzyl chloroformate (10.3 mL, 72.7 mmol) and 2 M NaOH solution (33 mL, 66 mmol) were simultaneously added dropwise to a stirred solution of 4-aminomethylbenzoic acid (29) (10.0 g, 66.2 mmol) in 2 M NaOH solution (33 mL) and THF (30 mL) at 0 C. The mixture was stirred at 20 C. for 16 h, then the organic solvent was evaporated and the residue acidified with 2 M HCl until the pH of the mixture was 2-3. The precipitate was filtered, washed with water (250 mL), washed with EtOH (50 mL), and finally washed with Et2O (100 mL). The solid was dried under vacuum to give acid 2 (16.43 g, 87%) as a white powder: mp 190-192 C. [lit. (Loge et. al., J. Enzyme Inhibit. Med. Chem. 2002, 17, 381-390) mp (toluene) 194-195 C.; 1H NMR δ 7.85 (br d, 2H, H-2, H-6), 7.82 (br t, J=6.1 Hz, 1H, NHCO2), 7.30-7.40 (m, 5H, H-2', H-3', H-4', H-5', H-6'), 7.27 (br d, J=8.2 Hz, 2H, H-3, H-5), 5.05 (s, 2H, OCH2), 4.24 (d, J=6.1 Hz, 2H, CH2N).
87%	With sodium hydroxide; In tetrahydrofuran; at 0 - 20℃; for 16h;	Benzylchloroformate (10.3 mL, 72.7 mmol) and 2 M NaOH solution (33 mL, 66 mmol) weresimultaneously added dropwise to a stirred solution of 4-aminomethylbenzoicacid (1) (10.0 g, 66.2 mmol) in 2 M NaOH solution (33 mL) and THF (30 mL) at 0C. The mixture was stirred at 20 C. for 16 h, then the organic solvent wasevaporated and the residue acidified with 2 M HCl until the pH of the mixturewas 2-3. The precipitate was filtered, washed with water (250 mL), washed withEtOH (50 mL), and finally washed with Et2O (100 mL). The solid was dried undervacuum to give acid 2 (16.43 g, 87%)

32%	With sodium hydrogencarbonate; In water; acetone; at 0 - 20℃;	4-(Aminomethyl)benzoic acid (4.53 g, 30.0 mmol) was dissolved in acetone (50 mL), sodium hydrogen carbonate (sat, 50 mL), and water (50 mL). After cooling to 0 C and an additional adding of ice (ca 10 mL) to the reaction mixture, benzyl chloroformate (4.5 mL, 31.5 mmol) in acetone (25 ml) was added dropwise. The mixture was allowed to attain room temperature and then stirred overnight. The mixture was diluted with water and washed with dichloromethane. The water layer was acidified with HCI (1 M) and extracted with ethyl acetate. The organic layer was basified with NaOH (aq) and a precipitate was formed. This was filtered off, washed with acetone and dichloromethane. Recrystallization from methanol yielded pure product (2.76 g, 9.67 mmol, 32%). 3C NMR (101 MHz, DMSO-cfe) δ ppm 43.77, 65.79, 127.31 , 128.01 , 128.16, 128.69, 129.45, 129.69, 137.32, 145.24, 156.72, 167.39
	With hydrogenchloride; In tetrahydrofuran; sodium hydroxide;	Step A. Preparation of 4-(N-CBz-aminomethyl)-benzoic acid 10.0 g (66 mmol) of 4-aminomethylbenzoic acid was dissolved in 33 ml of 2N NaOH solution (66 mmol) and 30 ml of THF. 12.45 g (73 mmol) of benzyl chloroformate and 37.5 ml of 2N NaOH solution was added in aliquots at 0 C. over 20 minutes. The reaction was stirred at room temperature over night and concentrated in vacuo to remove THF. 2N HCl was added to acidify to pH2-3. The precipitated solid was recovered by filtration and washed with ether to remove excess benzyl chloroformate. The solid was dried in vacuo to give 18.8 g of the desired product. 400 MHz 1H NMR (CD3OD): 4.31 (s, 2H); 5.09 (s, 2H); 7.30 (m, 7H); 7.91 (d, 2H).
	With potassium carbonate; In water; for 16h;	Compound 34 (4.00 g, 26.5 mmol) in aq. K2CO3 (1.0 M, 144 mL) was stirred vigorously with BnOCOCl (4.52 g, 26.5 mmol) for 16 h. The precipitate was collected by filtration and dried. This material was stirred with SOCl2 (10 mL) under Ar for 16 h. The evaporation residue was suspended in CH2Cl2 and filtered. Evaporation gave the crude acyl chloride, which was used immediately. This acyl chloride in dry THF (70 mL) was stirred with 2-aminobenzamide 12 (1.96 g, 14.4 mmol), pyridine (1.48 g, 18.7 mmol) and DMAP (0.35 g, 2.88 mmol) under Ar for 16 h. The evaporation residue, in EtOAc, was washed twice with water and twice with brine. Drying, evaporation and chromatography (EtOAc/CH2Cl2 2:3) gave 35 (5.1 g, 88%) as a white solid: mp 180-183 C;

References: [1]New Journal of Chemistry,2007,vol. 31,p. 623 - 627.
[2]Journal of the American Chemical Society,2003,vol. 125,p. 4420 - 4421.
[3]Journal of the American Chemical Society,2004,vol. 126,p. 12833 - 12842.
[4]Patent: WO2013/155338,2013,A2 .Location in patent: Page/Page column 116-117.
[5]Patent: US2015/329503,2015,A1 .Location in patent: Paragraph 0586.
[6]Patent: JP5789603,2015,B2 .Location in patent: Paragraph 0177.
[7]Angewandte Chemie - International Edition,2017,vol. 56,p. 11549 - 11553.
Angew. Chem.,2017,vol. 129,p. 11707 - 11711.
[8]Journal of labelled compounds and radiopharmaceuticals,2009,vol. 52,p. 316 - 323.
[9]Journal of labelled compounds and radiopharmaceuticals,2007,vol. 50,p. 395 - 398.
[10]Patent: WO2015/63694,2015,A1 .Location in patent: Page/Page column 34.
[11]Patent: US6191171,2001,B1 .
[12]Nucleosides, nucleotides and nucleic acids,2008,vol. 27,p. 495 - 505.
[13]ACS Medicinal Chemistry Letters,2013,vol. 4,p. 1173 - 1177.
[14]European Journal of Medicinal Chemistry,2016,vol. 118,p. 316 - 327.
[15]Angewandte Chemie - International Edition,2020,vol. 59,p. 18172 - 18178.
Angew. Chem.,2020,vol. 132,p. 18329 - 18335,7.

10
[ 58933-52-1 ]
[ 75-65-0 ]
[ 220851-46-7 ]

References: [1]Journal of labelled compounds and radiopharmaceuticals,2007,vol. 50,p. 395 - 398.
[2]Journal of labelled compounds and radiopharmaceuticals,2009,vol. 52,p. 316 - 323.

11
[ 58933-52-1 ]
[ 543-27-1 ]
C₂₁H₂₃NO₆ [ No CAS ]