Name: 18342-66-0|2,5-Dioxopyrrolidin-1-yl methylcarbamate|97%
Brand: Ambeed
SKU: A112581
Price: 5.0 USD
Availability: InStock
Rating: 96 (35 reviews)

1
[ 6066-82-6 ]
[ 624-83-9 ]
[ 18342-66-0 ]

Yield	Reaction Conditions	Operation in experiment
86%	With triethylamine; In ethyl acetate; at 0 - 20℃; for 24h;	A dried round-bottom flask was charged with N-hydroxysuccinimide (5.83 g, 50.7 mmol), ethyl acetate (20 mL) as a solvent and cooled at 0 C. To the mixture were slowly added triethylamine (4.76 g) and methylisocyanate (6.39 g, 0.112 mmol) at the same temperature. The reaction temperature was slowly raised to rt, and the mixture was stirred for 24 h at rt. After the volatile materials were removed under reduced pressure the crude residue was re-crystallized from ethyl acetate/diethyl ether to give 51a (86 %). Colorless needles, mp 148.0-149.0 C (lit [19]. 148.0-152.0C); 1H NMR (300 MHz, CDCl3): delta 8.15 (1H, br, NH), 2.76 (4H, s, CH2CH2), 2.67 (3H, s-like, CH3); 13C NMR (22.5 MHz, CDCl3): delta 170.66, 151.98, 27.98, 25.47; MS (FAB+) m/z 173 (M+H).

Reference： [1]European Journal of Medicinal Chemistry,2014,vol. 82,p. 16 - 35
[2]Journal of Medicinal Chemistry,1982,vol. 25,p. 178 - 182
[3]Journal of the American Chemical Society,1995,vol. 117,p. 1240 - 1245

2
[ 15149-73-2 ]
[ 593-51-1 ]
[ 18342-66-0 ]

Reference： [1]Synthesis,1993,p. 103 - 106

3
[ 18342-66-0 ]
[ 80354-48-9 ]

Yield	Reaction Conditions	Operation in experiment
73%	With sodium acetate; dinitrogen tetraoxide; In dichloromethane; at -40 - 20℃; for 2h;	A dried round-bottom flask was charged with sodium acetate (409 mg, 4.99 mmol), 51a (2.0 g, 8.0 mmol), and dichloromethane (25 mL) as a solvent, and a suspension of the mixture was stirred at-40 C. To the mixture, N2O4 (5.08 g, 55.2 mmol) in dichloromethane (10 mL) was added drop-by-drop with stirring. The mixture was stirred at-40 C for 1 h, and then the temperature was slowly raised to the room temperature followed by an additional 1 h stirring. The reaction mixture was poured into iced water, and an aqueous layer was extracted with dichloromethane. The combined organic layer was successively washed with 10 % NaHCO3 and a brine, and dried over Na2SO4 over-night in a refrigerator. To the concentrated filtrate (5 mL) was added petroleum ether to precipitate a crude product, which was recrystallized from chloroform/ether to give 51b (73 %). light yellow needles, mp not determined (lit [31]. 148-152C); 1H NMR (300 MHz, CDCl3): delta 3.22 (4H, s, CH2CH2), 2.95 (3H, s, CH3); 13C NMR (22.5 MHz, CDCl3): delta 168.53, 151.09, 28.44, 25.57.

Reference： [1]Journal of Medicinal Chemistry,1982,vol. 25,p. 178 - 182
[2]European Journal of Medicinal Chemistry,2014,vol. 82,p. 16 - 35

4
[ 74124-79-1 ]
[ 74-89-5 ]
[ 18342-66-0 ]
[ 96-31-1 ]

Reference： [1]Tetrahedron Letters,1983,vol. 24,p. 4569 - 4572

5
[ 18342-66-0 ]
[ 220472-67-3 ]
3-amino-9-N-(2-N'-methylureidoethyl)carbamoylethyl-β-carboline [ No CAS ]

Reference： [1]Heterocycles,1998,vol. 48,p. 2477 - 2480

7
[ 868840-76-0 ]
[ 18342-66-0 ]
cyclo(N^w-(N-methylcarbamoyl)-L-arginyl-N-methyl-L-phenylalanyl-β-L-aspartyl-β-L-aspartyl-D-alanyl) [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2005,vol. 15,p. 4717 - 4721

8
[ 18342-66-0 ]
[ 371123-22-7 ]
1-((2S,3R,4R,5S,6R)-4,5-Dihydroxy-6-hydroxymethyl-2-phenylsulfanyl-tetrahydro-pyran-3-yl)-3-methyl-urea [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry,2006,vol. 14,p. 2300 - 2313

9
[ 18342-66-0 ]
[ 70354-71-1 ]
[ 57-47-6 ]

Reference： [1]Chemistry - A European Journal,2007,vol. 13,p. 961 - 967
[2]European Journal of Organic Chemistry,2018,vol. 2018,p. 6671 - 6681

10
[ 857274-59-0 ]
[ 18342-66-0 ]
[ 857275-30-0 ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine; In DMF (N,N-dimethyl-formamide); at 20℃; for 2h;	a) Benzyl 3-{7-bromo-3-methyl-1-[2-(3-methylureido)ethyl]-1H-indol-6-ylmethoxy}-4-{4-[3-(2- methoxvbenzvioxy propoxy] phenvl} piperidine-1-carboxvlate The solution of 0.270 g of benzyl 3- [1- (2-aminoethyl)-7-bromo-3-methyl-1H-indol-6-ylmethoxy]-4- 4- [3- (2-methoxybenzyloxy) propoxy] phenyl} piperidine-1-carboxylate (Example 76b) in 1.5 mi of N, N- dimethylformamide is cooled to 0C and admixed successively with 0.066 g of N-succinimidyl N- methyl carbamate and 0.043 ml of triethylamine. The reaction mixture is stirred at room temperature over 2 hours, subsequently poured onto water (40 mi) and extracted with dichloromethane (2 x 40 ml). The organic phases are washed successively with water (40 ml), 1 M sodium hydrogencarbonate solution (40 mi) and brine (40 ml), dried over sodium sulphate, filtered and concentrated by evaporation. The title compound is obtained as a brown oil from the residue by means of flash chromatography (SiO2 60F). Rf = 0.10 (2: 1 EtOAc-heptane); Rt = 5.76.

Reference： [1]Patent: WO2005/61457,2005,A1 .Location in patent: Page/Page column 85-86

11
[ 18342-66-0 ]
[ 94838-55-8 ]
[ 903556-24-1 ]

Yield	Reaction Conditions	Operation in experiment
96%	With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20℃; for 72h;	To a solution of commercially available (4-amino-benzyl)-carbamic acid tert- butyl ester (229 mg) in dry dichloromethane (1 mL) were successively added ethyl diisopropyl amine (349 muL) and N-succinimidyl N-methylcarbamate (355 mg). The resulting reaction mixture was stirred at room temperature for 72 h, then diluted with ethyl acetate (20 mL) and washed with 0.1 M aqueous sodium hydroxide (3×10 mL). The combined organic layer were dried (MgSO4), filtered and concentrated to afford the title compound (269 mg; 96%). [MH]+=280, [MNa]+=302.

Reference： [1]Patent: US2006/173183,2006,A1 .Location in patent: Page/Page column 87-88

12
[ 18342-66-0 ]
[ 147291-66-5 ]
[ 903556-18-3 ]

Yield	Reaction Conditions	Operation in experiment
80%	With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20℃; for 72h;	To a solution of commercially available (3-amino-benzyl)-carbamic acid tert- butyl ester (222 mg) in dry dichloromethane (1 mL) were successively added ethyl diisopropyl amine (349 muL) and N-succinimidyl N-methylcarbamate (355 mg). The resulting reaction mixture was stirred at room temperature for 72 h, then diluted with ethyl acetate (20 mL) and washed with 0.1 M aqueous sodium hydroxide (3×10 mL). The combined organic layer were dried (MgSO4), filtered and concentrated. The remaining residue was purified by flash chromatography (silica, dichloromethane/methanol) to afford the title compound (223 mg; 80%). [MH]+=280, [MNa]+=302.

Reference： [1]Patent: US2006/173183,2006,A1 .Location in patent: Page/Page column 86

13
(1RS,3SR)-1-(3-hydroxy-phenyl)-3-methyl-2,3,4,9-tetrahydro-1H-β-carboline-3-carboxylic acid methyl ester [ No CAS ]
[ 18342-66-0 ]
(+/-)-(3aSR,10RS)-10-(3-hydroxy-phenyl)-2,3a-dimethyl-3a,4,9,10-tetrahydro-2,9,10a-triaza-cyclopenta[b]fluorene-1,3-dione [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
25%	In water; acetonitrile; at 150℃; for 0.0833333h;Irradiation;	Examples Final compounds .3aSR,10RS)-10-(3-Hydroxy-phenyl)-2,3a-dimethyl-3a,4,9,10-tetrahydro-2,9,10a-triaza-cyclopenty[b]fluorene-1,3-dioneTo a suspension of 250 mg (740 \|jmol) RS,3SR)-1-(3-hydroxy-phenyl)-3-methyl-2,3,4,9-tetrahydro-1 H-p-carboline-3-carboxylic acid methyl ester (compound A1) in 4 ml acteonitrile and 1 ml water are added 511 mg (3 mmol) N-succinimidyl-N-methylcarbamate. The mixture is heated to 150 C for 5 min using a microwave reactor. The solvents are removed under reduced pressure. The residue is dissolved in ethyl acetate and the organic layer is washed with water. The solution is dried with magnesium sulfate and the solvent is removed under reduced pressure. After column chromatography (toluene, ethyl acetate 4:1), 68 mg (25 %) of the title compound are obtained as a white solid (m.p.: 299-305 C; m/z (MH+) = 362.2).

Reference： [1]Patent: WO2006/18435,2006,A1 .Location in patent: Page/Page column 23

14
[ 876666-00-1 ]
[ 18342-66-0 ]
(3aR,10R)-10-(3-hydroxy-phenyl)-2-methyl-4,10-dihydro-3aH-9-thia-2,10-diaza-cyclopenta[b]fluorene-1,3-dione [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In acetone; at 150℃; for 0.0833333h;Irradiation;	A3. (3aR,10R)-10-(3-Hydroxy-phenyl)-2-methyl-4,10-dihydro-3aH-9-thia-2,10-diaza-cyclopenta[b]fluorene-1,3-dione405 mg (2.35 mmol) of N-succinimidyl-N-methyl carbamate are added to a solution of 200 mg (590 \|jmol) of (1 R,3R)-1-(3-hydroxy-phenyl)-1,2,3,4-tetrahydro-benzo[4,5]thieno[2,3-c]pyridine-3-carboxylic acid methyl ester (compound A4) in 4 ml of acetone. The mixture is heated to 150C for 5 min. using a microwave reactor. The solvent is removed under reduced pressure. The crude product obtained can be used as starting material to obtain compound 3.

Reference： [1]Patent: WO2006/18435,2006,A1 .Location in patent: Page/Page column 25

15
[ 18342-66-0 ]
(1RS,3SR)-6-ethoxy-1-(3-hydroxy-phenyl)-3-methyl-2,3,4,9-tetrahydro-1H-β-carboline-3-carboxylic acid methyl ester [ No CAS ]
(3aSR,10RS)-6-ethoxy-10-(3-hydroxy-phenyl)-2,3a-dimethyl-3a,4,9,10-tetrahydro-2,9,10a-triaza-cyclopenta[b]fluorene-1,3-dione [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In water; acetonitrile; at 150℃; for 0.5h;Microwave irradiation;	1. (SaSR.IORSJ-e-Ethoxy-IO-CS-hydroxy-phenyO^.Sa-dimethyl-Salambdatheta.IO-tetrahydro^.theta.iOa- triaza-cyclopenta[b]fluorene-1,3-dione; A solution of 125 mg (1 RS,3SR)-6-ethoxy-1-(3-hydroxy-phenyl)-3-methyl-2,3,4,9-tetrahydro-1 H-beta- carboline-3-carboxylic acid methyl ester and 226 mg N-succinimidyl-N-methylcarbamate in a mixture of 5 ml acetonitrile and 1 ml water is heated to 150 0C for 30 min using a microwave reactor. Water and ethylacetate are added to the solution. The aqueous phase is extracted with ethylacetate and the combined organic layers are dried with magnesium sulfate. The solvents are removed under reduced pressure. After purification by column chromatography (toluene/ethylactate 4:1 ) 15 mg of the title compound are obtained as a colorless foam (MS: m/z (MH+) = 406.1 ).

Reference： [1]Patent: WO2007/96393,2007,A1 .Location in patent: Page/Page column 121

16
[ 18342-66-0 ]
(1RS,3SR)-6-methoxy-3-methyl-1-phenyl-2,3,4,9-tetrahydro-1H-β-carboline-3-carboxylic acid methyl ester [ No CAS ]
(3aSR,10RS)-6-methoxy-2,3a-dimethyl-10-phenyl-3a,4,9,10-tetrahydro-2,9,10a-triaza-cyclopenta[b]fluorene-1,3-dione [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In water; acetonitrile; at 150℃; for 0.5 - 0.666667h;microwave irradiation;	2. (3aSR,10RS)-6-Methoxy-2,3a-dimethyl-10-phenyl-3a, 4,9,10-tetrahydro-2, 9,10a-triaza- cyclopenta[b]fluorene-1,3-dione; A solution of (I RS.SSRJ-e-methoxy-S-methyl-i-phenyl^.S^.theta-tetrahydro-I H-beta-carboline-S-carboxylic acid methyl ester and N-succinimidyl-N-methylcarbamate in a mixture of acetonitrile and water (5:1 ) is heated to 150 0C for 30 min using a microwave reactor.Water and ethylacetate are added to the solution. The aqueous phase is extracted with ethylacetate and the combined organic layers are dried with magnesium sulfate. The solvents are removed under reduced pressure. After purification by column chromatography the title compound will be obtained. In more detail, the title compound can be obtained as follows: To a suspension of 200 mg (1 RS, 3SR)- 6-Methoxy-3-methyl-1-phenyl-2,3,4,9-tetrahydro-1 H-beta-carboline-3-carboxylic acid methyl ester in a mixture of 4 ml acetonitrile and 1 ml water are added 395 mg N-succinimidyl N-methyl carbamate. The mixture is heated in a sealed tube for 40 min to 150 0C using a microwave reactor. After cooling to room temperature water and brine is added and the mixture is extracted with ethyl acetate. The combined organic layers are dried with magnesium sulfate and the solvent is removed under reduced <n="90"/>pressure. After purification of the residue by column chromatography (silica gel, toluene/ethyl acetate) and triturating with diisopropyl ether, 65 mg of the title compound are obtained. MS: m/z (MH+) = 376.1

Reference： [1]Patent: WO2007/96395,2007,A1 .Location in patent: Page/Page column 88-89

17
[ 18342-66-0 ]
[ 1096164-95-2 ]
[ 1096165-07-9 ]

Yield	Reaction Conditions	Operation in experiment
	In acetonitrile; for 96h;Heating / reflux;	A mixture of (S)-3-(3-benzyloxy-4-hydroxy-phenyl)-2-tert-butoxycarbonylamino- propionic acid methyl ester (1.15g, 2.87mmol) and N-succinimidyl N- methylcarbamate (1.975g, 11.47mmol) in acetonitrile (15mL) was refluxed 4 days. After the removal of solvent, the residue was purified with chromatography using EtOAc/hexane(1 :1.5) as an eluent to obtain (S)-3-(3-benzyloxy-4- methylcarbamoyloxy-phenyl)-2-tert-butoxycarbonylamino-propionic acid methyl ester as a white solid, 0.83g. 1H NMR (400MHz, CDCI3) 1.43 (s, 9H), 2.86 (d, 3H), 3.03 (m, 2H), 3.66 (s, 3H), 4.56 (m, 1 H), 4.98 (m, 2H), 5.05 (s, 2H), 6.70-6.90 (m, 2H), 7.03 (m, 1H), 7.29-7.43 (m, 5H).

Reference： [1]Patent: WO2009/7696,2009,A1 .Location in patent: Page/Page column 31

18
[ 18342-66-0 ]
[ 367967-67-7 ]
[ 1096165-04-6 ]

Yield	Reaction Conditions	Operation in experiment
	In acetonitrile; for 96h;Heating / reflux;	N-Succinimidyl N-methylcarbamate (1.89g, 11 mmol) was added to a solution of (S)- 3-(4-Benzyloxy-3-hydiOxy-phenyl)-2-tert-butoxycarbonylamino-propionic acid methyl ester (1.1g, 2.74 mmol) in acetonitrile (15ml). The mixture was refluxed 4 days. After removal of the solvent, the residue was purified by silica gel chromatography eluting with ethyl acetate/hexane (2:3). (S)-3-(4-Benzyloxy-3-methylcarbamoyloxy-phenyl)-2- tert-butoxycarbonylamino-propionic acid methyl ester was obtained as a white solid, 0.83g. 1 H NMR (400MHz, CDCI3) 1.42 (s, 9H), 2.86 (d, J = 4.9Hz, 3H), 3.01 (m, 2H), 3.70 (s, 3H), 4.53 (m, 1 H), 5.00 (m, 2H), 5.07 (s, 2H), 6.89 (m, 3H), 7.29-7.42 (m, 5H).

Reference： [1]Patent: WO2009/7696,2009,A1 .Location in patent: Page/Page column 29

19
[ 18342-66-0 ]
(1RS,3RS)-6-fluoro-1-(3-hydroxy-phenyl)-2,3,4,9-tetrahydro-1H-β-carboline-3-carboxylic acid methyl ester [ No CAS ]
(1RS,3SR)-6-fluoro-1-(3-hydroxy-phenyl)-2,3,4,9-tetrahydro-1H-β-carboline-3-carboxylic acid methyl ester [ No CAS ]
(3aSR,10RS)-6-fluoro-10-(3-hydroxy-phenyl)-2-methyl-3a,4,9,10-tetrahydro-2,9,10a-triaza-cyclopenta[b]fluorene-1,3-dione [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		To a solution of the crude mixture of (1 RS,3RS)-6-fluoro-1-(3-hydroxy-phenyl)-2,3,4,9-tetrahydro- 1 H-beta-carboline-3-carboxylic acid methyl ester and (1 RS,3SR)-6-fluoro-1-(3-hydroxy-phenyl)- 2,3,4,9-tetrahydro-1 H-beta-carboline-3-carboxylic acid methyl ester in 10 ml acetone are added 1.34 g (7.80 mmol) N-succinimidyl-N-methylcarbamate. The mixture is heated to 150 0C for 20 min using a microwave reactor. The solvent is removed at reduced pressure and the residue is dissolved in 20 ml acetonitrile. 2.7 g potassium carbonate are added and the suspension is heated to reflux for 210 min. The solvent is removed at reduced pressure and the residue is dissolved in ethyl acetate. The solution is washed with water and brine. The organic layer is dried with magnesium sulfate and the solvent is removed at reduced pressure. The crude product is suspended in a mixture of methanol and dichloromethane and heated to reflux. After cooling to room temperature the desired product is filtered from the suspension and dried. 460 mg of the title compound are obtained as a colourless solid. m.p.: 328-331 0CMF: C20 H16 F N3 03 (365.37) MS: m/z (M-H+) = 364,1

Reference： [1]Patent: WO2009/24190,2009,A1 .Location in patent: Page/Page column 45

20
[ 18342-66-0 ]
(1RS,3RS)-1-(3-hydroxy-phenyl)-6-methoxy-2,3,4,9-tetrahydro-1H-β-carboline-3-carboxylic acid methyl ester [ No CAS ]
(1RS,3SR)-1-(3-hydroxy-phenyl)-6-methoxy-2,3,4,9-tetrahydro-1H-β-carboline-3-carboxylic acid methyl ester [ No CAS ]
(3aSR,10RS)-10-(3-hydroxy-phenyl)-6-methoxy-2-methyl-3a,4,9,10-tetrahydro-2,9,10a-triaza-cyclopenta[b]fluorene-1,3-dione [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
48%		To a solution of the mixture of (1 RS,3RS)-6-methoxy-1-(3-hydroxy-phenyl)-2,3,4,9-tetrahydro-1 H- beta-carboline-3-carboxylic acid methyl ester and (1 RS,3SR)-6-methoxy-1-(3-hydroxy-phenyl)- 2,3,4,9-tetrahydro-1 H-beta-carboline-3-carboxylic acid methyl ester in 10 ml acetone are added 156 mg (900 mumol, 4.00 eq) N-succinimidyl-N-methylcarbamate. The mixture is heated to 150 0C for 10 min using a microwave reactor. The solvent is removed at reduced pressure and the residue is dissolved in 5 ml acetonitrile. 313 mg potassium carbonate are added and the suspension is heated to reflux for 150 min. The solvent is removed at reduced pressure and the residue is dissolved in ethyl acetate. The solution is washed with water and brine. The organic layer is dried with magnesium sulfate and the solvent is removed at reduced pressure. After column chromatography (silica gel, toluene/ethyl acetate 4:1 ) 42 mg (48 %) of the desired product are obtained as a pale solid, m.p.: 172-175 0C; MF: C21 H19 N3 04 (377.40) MS: m/z (MH+) = 378.2.

Reference： [1]Patent: WO2009/24190,2009,A1 .Location in patent: Page/Page column 46

21
[ 18342-66-0 ]
C₃₄H₅₁N₆O₁₀Pol [ No CAS ]
[ 4023-02-3 ]
C₃₇H₅₆N₉O₁₁Pol [ No CAS ]