86688-96-2|2-(1H-Pyrrol-3-yl)acetic acid| Ambeed

* 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 [ 86688-96-2 ]

[ 86688-96-2 ] Synthesis Path-Downstream 1~53

1
[ 33941-15-0 ]
[ 86688-96-2 ]
N-pyrrol 3-ylacetyl monoaza 18-crown-6 [ No CAS ]

References: [1]Journal of the Chemical Society. Chemical communications,1993,p. 1550 - 1552.

2
[ 109-97-7 ]
[ 104-87-0 ]
[ 86688-96-2 ]
((4Z,10Z,15Z,19Z)-5,10,15,20-Tetra-p-tolyl-22,24-dihydro-porphin-2-yl)-acetic acid [ No CAS ]

References: [1]Bulletin of the Chemical Society of Japan,1991,vol. 64,p. 2300 - 2302.

3
[ 109-97-7 ]
[ 86688-96-2 ]
[ 100-52-7 ]
((4Z,10Z,15Z,19Z)-5,10,15,20-Tetraphenyl-22,24-dihydro-porphin-2-yl)-acetic acid [ No CAS ]

References: [1]Bulletin of the Chemical Society of Japan,1991,vol. 64,p. 2300 - 2302.

4
[ 2788-84-3 ]
[ 86688-96-2 ]
[ 132081-32-4 ]

References: [1]Journal de Chimie Physique et de Physico-Chimie Biologique,1992,vol. 89,p. 1131 - 1136.

5
[ 4070-48-8 ]
[ 86688-96-2 ]
[ 132081-34-6 ]

References: [1]Journal de Chimie Physique et de Physico-Chimie Biologique,1992,vol. 89,p. 1131 - 1136.

6
[ 15411-43-5 ]
[ 86688-96-2 ]
[ 134226-30-5 ]

References: [1]Bulletin of the Chemical Society of Japan,1991,vol. 64,p. 1066 - 1068.

7
[ 1520-21-4 ]
[ 86688-96-2 ]
[ 134226-28-1 ]

References: [1]Bulletin of the Chemical Society of Japan,1991,vol. 64,p. 1066 - 1068.

8
[ 1592-20-7 ]
[ 86688-96-2 ]
[ 134226-20-3 ]

References: [1]Bulletin of the Chemical Society of Japan,1991,vol. 64,p. 1066 - 1068.

9
[ 86688-97-3 ]
[ 86688-96-2 ]

References: [1]Journal of Organic Chemistry,1983,vol. 48,p. 3214 - 3219.

10
[ 41775-76-2 ]
[ 86688-96-2 ]
N-pyrrol-3-ylacetyl monoaza 12-crown-4 [ No CAS ]

References: [1]Journal of the Chemical Society. Chemical communications,1993,p. 1550 - 1552.

11
[ 86688-96-2 ]
[ 50-00-0 ]

References: [1]Pharmazie,1990,vol. 45,p. 403 - 407.

12
[ 86688-96-2 ]
[ 24461-61-8 ]
[ 132081-36-8 ]

References: [1]Journal de Chimie Physique et de Physico-Chimie Biologique,1992,vol. 89,p. 1131 - 1136.

13
[ 771-61-9 ]
[ 86688-96-2 ]
pentafluorophenyl 1H-pyrrole-3-acetate [ No CAS ]

References: [1]Journal of the Chemical Society. Chemical communications,1995,p. 1471 - 1474.

14
[ 111-77-3 ]
[ 86688-96-2 ]
(1H-pyrrol-3-yl)acetic acid 2-(2-methoxyethoxy)ethyl ester [ No CAS ]

References: [1]Synthetic Communications,1996,vol. 26,p. 1289 - 1304.
[2]Journal of Materials Chemistry,1996,vol. 6,p. 1107 - 1112.

15
[ 1565-80-6 ]
[ 86688-96-2 ]
(1H-Pyrrol-3-yl)-acetic acid (S)-2-methyl-butyl ester [ No CAS ]

References: [1]Synthetic Communications,1996,vol. 26,p. 1289 - 1304.

16
[ 109-86-4 ]
[ 86688-96-2 ]
(1H-pyrrol-3-yl)acetic acid 2-methoxyethyl ester [ No CAS ]

References: [1]Synthetic Communications,1996,vol. 26,p. 1289 - 1304.
[2]Journal of Materials Chemistry,1996,vol. 6,p. 1107 - 1112.

17
[ 75-89-8 ]
[ 86688-96-2 ]
(1H-pyrrol-3-yl)acetic acid 2,2,2-trifluoroethyl ester [ No CAS ]

References: [1]Synthetic Communications,1996,vol. 26,p. 1289 - 1304.
[2]Journal of Materials Chemistry,1996,vol. 6,p. 1107 - 1112.

18
[ 375-01-9 ]
[ 86688-96-2 ]
(1H-pyrrol-3-yl)acetic acid 2,2,3,3,4,4,4-heptafluorobutyl ester [ No CAS ]

References: [1]Synthetic Communications,1996,vol. 26,p. 1289 - 1304.
[2]Journal of Materials Chemistry,1996,vol. 6,p. 1107 - 1112.

19
[ 86688-96-2 ]
2-(3-methylsulfanylpropylsulfanyl)ethanol [ No CAS ]
(1H-pyrrol-3-yl)acetic acid 2-(3-methylsulfanylpropylsulfanyl)ethyl ester [ No CAS ]

References: [1]Journal of Materials Chemistry,1996,vol. 6,p. 1107 - 1112.
[2]Synthetic Communications,1996,vol. 26,p. 1289 - 1304.

20
[ 138779-98-3 ]
[ 86688-96-2 ]

Yield	Reaction Conditions	Operation in experiment
94%		2.87 mL NaOH (5 N) in 2.30 mL methanol was added to N-tosyl-3-methylacetatel pyrrole 10 (260.8 mg, 0.89 mmol) and refluxed for 2 h. The methanol was removed and the residue was washed with diethyl ether and acidified by using a gradient of aqueous HCl in the range of 5 N-0.5 N to pH 3, and finally extracted four times with diethyl ether. The solution was dried over Na2SO4 anhydrous. After removal of the solvent, 3-acetic acid pyrrole 11 was obtained as a white solid (yield 105 mg, 0.84 mmol, 94%). The product was recognized by 1H NMR spectra [16] .

References: [1]European Journal of Medicinal Chemistry,2012,vol. 57,p. 391 - 397.
[2]Synthetic Communications,1996,vol. 26,p. 1289 - 1304.
[3]Macromolecules,2010,vol. 43,p. 9365 - 9370.

21
[ 137-32-6 ]
[ 86688-96-2 ]
(1H-pyrrol-3-yl)acetic acid 2-methylbutyl ester [ No CAS ]

References: [1]Journal of Materials Chemistry,1996,vol. 6,p. 1107 - 1112.

22
[ 86688-96-2 ]
[ 111-27-3 ]
(1H-pyrrol-3-yl)acetic acid hexyl ester [ No CAS ]

References: [1]Journal of Materials Chemistry,1996,vol. 6,p. 1107 - 1112.

23
[ 86688-96-2 ]
[ 530-62-1 ]
1-imidazol-1-yl-2-(1<i>H</i>-pyrrol-3-yl)-ethanone [ No CAS ]

References: [1]Journal of the Chemical Society. Perkin transactions I,1999,p. 1657 - 1664.

24
[ 186581-53-3 ]
[ 86688-96-2 ]
1-diazo-(3-pyrrolyl)-2-propanone [ No CAS ]

References: [1]Tetrahedron,2000,vol. 56,p. 8063 - 8069.

25
[ 86688-96-2 ]
4,6-dihydrocyclopenta[b]pyrrol-5(1H)-one [ No CAS ]

References: [1]Tetrahedron,2000,vol. 56,p. 8063 - 8069.

26
[ 86688-96-2 ]
Pyrrol-3-ylacetyl L-histidine methyl ester [ No CAS ]

References: [1]Journal of the Chemical Society. Perkin transactions I,1999,p. 1657 - 1664.

27
[ 106058-85-9 ]
[ 86688-96-2 ]

References: [1]Synthetic Communications,1996,vol. 26,p. 1289 - 1304.
[2]Macromolecules,2010,vol. 43,p. 9365 - 9370.
[3]European Journal of Medicinal Chemistry,2012,vol. 57,p. 391 - 397.

28
[ 86688-96-2 ]
2-((4Z,10Z,15Z,19Z)-5,10,15,20-Tetraphenyl-22,24-dihydro-porphin-2-yl)-N-(3-vinyl-phenyl)-acetamide [ No CAS ]

References: [1]Bulletin of the Chemical Society of Japan,1991,vol. 64,p. 2300 - 2302.

29
[ 86688-96-2 ]
2-((4Z,10Z,15Z,19Z)-5,10,15,20-Tetraphenyl-22,24-dihydro-porphin-2-yl)-N-(4-vinyl-phenyl)-acetamide [ No CAS ]

References: [1]Bulletin of the Chemical Society of Japan,1991,vol. 64,p. 2300 - 2302.

30
[ 86688-96-2 ]
((4Z,10Z,15Z,19Z)-5,10,15,20-Tetra-p-tolyl-22,24-dihydro-porphin-2-yl)-acetic acid 4-vinyl-benzyl ester [ No CAS ]

References: [1]Bulletin of the Chemical Society of Japan,1991,vol. 64,p. 2300 - 2302.

31
[ 86688-96-2 ]
((4Z,10Z,15Z,19Z)-5,10,15,20-Tetraphenyl-22,24-dihydro-porphin-2-yl)-acetic acid; compound with triethyl-amine [ No CAS ]

References: [1]Bulletin of the Chemical Society of Japan,1991,vol. 64,p. 2300 - 2302.

32
[ 86688-96-2 ]
((4Z,10Z,15Z,19Z)-5,10,15,20-Tetra-p-tolyl-22,24-dihydro-porphin-2-yl)-acetic acid; compound with triethyl-amine [ No CAS ]

References: [1]Bulletin of the Chemical Society of Japan,1991,vol. 64,p. 2300 - 2302.

33
[ 81453-98-7 ]
[ 86688-96-2 ]

References: [1]Journal of Organic Chemistry,1983,vol. 48,p. 3214 - 3219.

Yield	Reaction Conditions	Operation in experiment
70%		Preparation of (3-pyrrolyl)acetic acid: In a 100-cm3 flask equipped with a condenser, the above-mentioned product (10.5 mmoles) was introduced together with 30 cm3 of methanol. Next, 30 cm3 of a 5N sodium hydroxide aqueous solution was added thereto, and reaction was then carried out under reflux for 2.5 hours. Afterward, the solvent was evaporated, and the aqueous phase was washed with ethyl acetate, acidified to pH 3 with concentrated hydrochloric acid (10 cm3), and then extracted with diethyl ether. The used solvent was evaporated from the organic phase under reduced pressure in order to obtain 0.93 g of brown crystals (molecular weight=125; yield=70%). Melting point=90 C. NMR (DMSOd6) ppm 12.0 1H; 10.6 1H; 6.7 2H; 6.0 1H; 3.36 s 2H. IR (cm-1) 3383, 1696, 1416, 1399, 1340, 1279, 1212, 1071.

35
[ 877455-69-1 ]
[ 86688-96-2 ]
[ 1253640-94-6 ]

References: [1]Macromolecules,2010,vol. 43,p. 9365 - 9370.

36
[ 1253640-90-2 ]
[ 86688-96-2 ]
[ 1253640-92-4 ]

References: [1]Macromolecules,2010,vol. 43,p. 9365 - 9370.

37
[ 552888-06-9 ]
[ 86688-96-2 ]
[ 1253640-93-5 ]

References: [1]Macromolecules,2010,vol. 43,p. 9365 - 9370.

38
[ 16130-32-8 ]
[ 86688-96-2 ]
[ 1414702-04-7 ]

Yield	Reaction Conditions	Operation in experiment
62%	With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; at 20.0℃;	EDCI (183 mg, 1.0 mmol), DMAP (6 mg, 0.05 mmol), and 12 (168 mg, 0.3 mmol) were added to a solution of <strong>[86688-96-2]2-<strong>[86688-96-2](1H-pyrrol-3-yl)acetic acid</strong></strong> 11 (54 mg, 0.4 mmol) in dichloromethane (1.2 mL) and stirred overnight at r.t.. Upon dilution with water, the aqueous solution was extracted with dichloromethane (4 × 4 mL). The combined organic layer was washed with water (4 mL), dried (Na2SO4), filtered, and the solvent concentrated in vacuo. The residue was chromatographed on silica gel (hexane/ethyl acetate = 7/3) to afford the esters 13 as a yellow oil (yield 120 mg, 0.3 mmol, 62%); Rf = 0.38 (hexane/ethyl acetate, 6/4). 1H NMR (CDCl3, 300 MHz, 25 C): delta = 2.32 (s, 3H, CH3CN); 3.00 (t, J = 7.2 Hz, 2H, CCH2CH2O); 3.51 (s, 2H, CCH2CO); 3.84 (s, 3H, OCH3); 4.29 (t, J = 7.2 Hz, 2H, CCH2CH2O); 6.13-6.15 (m, 1H, CHarom); 6.65-6.68 (m, 2H, CHarom); 6.71-6.73 (m, 1H, CHarom); 6.89 (d, J = 8.6 Hz, 1H, CHarom); 6.97 (d, J = 2.5 Hz, 1H, CHarom); 7.45-7.48 (m, 2H, CHarom); 7.62-7.65 (m, 2H, CHarom); 8.11 (bs, 1H, NH). 13C NMR (CDCl3, 75 MHz, 25 C): delta = 13.1; 23.7; 33.0; 55.7; 63.5; 101.3; 109.1; 111.4; 114.9; 115.3; 115.4; 116.5; 118.0; 129.0; 130.9; 131.0; 131.0; 134.1; 135.2; 139.0; 156.0; 168.2; 172.4. HRMS: calcd. for [C25H23ClN2O4 + Na]+ 473.1239; found 473.1245. IR (CHCl3): nu?=3481,nu?=3481,1730, 1674 cm-1. M.p.: 90-92 C.

References: [1]European Journal of Medicinal Chemistry,2012,vol. 57,p. 391 - 397.

39
[ 87630-41-9 ]
[ 86688-96-2 ]