[ CAS No. 185116-43-2 ] {[proInfo.proName]}

Name: 185116-43-2|Fmoc-4-Abz-OH|97%
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Quality Control of [ 185116-43-2 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 185116-43-2 ]

Product Details of [ 185116-43-2 ]

CAS No. :	185116-43-2	MDL No. :	MFCD00144888
Formula :	C₂₂H₁₇NO₄	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	VGSYYBSAOANSLR-UHFFFAOYSA-N
M.W :	359.37	Pubchem ID :	2756082
Synonyms :

Safety of [ 185116-43-2 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P280-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 185116-43-2 ]

* 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.

Upstream synthesis route of [ 185116-43-2 ]
Downstream synthetic route of [ 185116-43-2 ]

[ 185116-43-2 ] Synthesis Path-Upstream 1~2

1
[ 28920-43-6 ]
[ 150-13-0 ]
[ 185116-43-2 ]

Yield	Reaction Conditions	Operation in experiment
94%	for 24 h; Inert atmosphere	p-Aminobenzoic acid (10 g, 73 mmol) was dissolved in dry NMP (50 ml) under an inert atmosphere followed by the dropwise addition of Fmoc-Cl (18.9 g, 73 mmol) in dry NMP (50 ml). After 24 hrs, the reaction mixture was poured slowly into 400 ml water. The colorless precipitate was collected by filtration, washed with water and dried in vacuum at 120 ºC to give N‐Fmoc-p-amino benzoic acid (24.8 g, 94percent). mp: 215 ºC (dec.) 1H-NMR: δ (300 MHz, DMSO-d6) 4.33 (t, 3J = 6.25 Hz, 1 H); 4.54 (d, 3J = 6.25 Hz, 2 H); 7.33-7.45 (m, 4 H); 7.57 (d, 3J = 7.35 Hz, 2 H); 7.76 (d, 3J = 7.35 Hz, 2 H); 7.89 (m, 4 H), 10.08 (s, 1H); 12.69 (s, 1H). 13C-NMR and DEPT: δ (300 MHz, DMSO-d6) 46.61 (+); 65.83 (-); 117.5 (+); 120.22 (+); 124.48; 125.14 (+); 127.17 (+); 127.74 (+); 130.48 (+); 140.86; 143.31; 143.74; 153.31; 167.03. IR ν (cm-‐1): 3344, 2970, 2887, 2660, 2544, 1709, 1673, 1610, 1592, 1526, 1511, 1411, 1311, 1282, 1221, 1052, 850, 736. RP-HPLC (min): 26.6 min. M (FD): m/z (percent) = 359.1 (100); 360.1 (17.4); calc.[C22H17NO4] = 359.1

Reference： [1] Tetrahedron Letters, 2013, vol. 54, # 8, p. 753 - 756
[2] Chemical Communications, 2013, vol. 49, # 40, p. 4555 - 4557
[3] Journal of Chemical Research, Miniprint, 1998, # 10, p. 2736 - 2753
[4] Chemical Communications, 2014, vol. 50, # 14, p. 1691 - 1693

2
[ 82911-69-1 ]
[ 150-13-0 ]
[ 185116-43-2 ]

Reference： [1] European Journal of Organic Chemistry, 2008, # 9, p. 1582 - 1588
[2] Biological Chemistry, 2015, vol. 396, # 1, p. 45 - 52

[ 185116-43-2 ] Synthesis Path-Downstream 1~76

1
[ 145013-05-4 ]
[ 185116-43-2 ]
4-(amidinoamino)benzamide [ No CAS ]

Reference： [1]Tetrahedron,1997,vol. 53,p. 6697 - 6705

2
[ 152120-54-2 ]
[ 185116-43-2 ]
4-(amidinoamino)benzamide [ No CAS ]

Reference： [1]Tetrahedron,1997,vol. 53,p. 6697 - 6705

3
[ 112883-29-1 ]
[ 135273-01-7 ]
[ 185116-43-2 ]
(4R,9R)-4-[(S)-2-Amino-3-(4-hydroxy-phenyl)-propionylamino]-3,11-dioxo-6,7-dithia-2,10-diaza-bicyclo[10.2.2]hexadeca-1⁽¹⁵⁾,12⁽¹⁶⁾,13-triene-9-carboxylic acid [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,1997,vol. 40,p. 3359 - 3368

4
[ 35661-40-6 ]
[ 119831-72-0 ]
[ 135673-97-1 ]
[ 185116-43-2 ]
4-Amino-N-{(S)-1-[(S)-1-((S)-1-carbamoyl-2-phenyl-ethylcarbamoyl)-4-guanidino-butylcarbamoyl]-2-cyclohexyl-ethyl}-benzamide [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,1999,vol. 9,p. 1423 - 1428

5
[ 3140-73-6 ]
[ 185116-43-2 ]
4-(9<i>H</i>-fluoren-9-ylmethoxycarbonylamino)-benzoic acid 4,6-dimethoxy-[1,3,5]triazin-2-yl ester [ No CAS ]

Reference： [1]Journal of Chemical Research, Miniprint,1998,p. 2736 - 2753

6
[ 28920-43-6 ]
[ 150-13-0 ]
[ 185116-43-2 ]

Yield	Reaction Conditions	Operation in experiment
94%	for 24h;Inert atmosphere;	p-Aminobenzoic acid (10 g, 73 mmol) was dissolved in dry NMP (50 ml) under an inert atmosphere followed by the dropwise addition of Fmoc-Cl (18.9 g, 73 mmol) in dry NMP (50 ml). After 24 hrs, the reaction mixture was poured slowly into 400 ml water. The colorless precipitate was collected by filtration, washed with water and dried in vacuum at 120 ºC to give N-Fmoc-p-amino benzoic acid (24.8 g, 94%). mp: 215 ºC (dec.) 1H-NMR: delta (300 MHz, DMSO-d6) 4.33 (t, 3J = 6.25 Hz, 1 H); 4.54 (d, 3J = 6.25 Hz, 2 H); 7.33-7.45 (m, 4 H); 7.57 (d, 3J = 7.35 Hz, 2 H); 7.76 (d, 3J = 7.35 Hz, 2 H); 7.89 (m, 4 H), 10.08 (s, 1H); 12.69 (s, 1H). 13C-NMR and DEPT: delta (300 MHz, DMSO-d6) 46.61 (+); 65.83 (-); 117.5 (+); 120.22 (+); 124.48; 125.14 (+); 127.17 (+); 127.74 (+); 130.48 (+); 140.86; 143.31; 143.74; 153.31; 167.03. IR nu (cm--1): 3344, 2970, 2887, 2660, 2544, 1709, 1673, 1610, 1592, 1526, 1511, 1411, 1311, 1282, 1221, 1052, 850, 736. RP-HPLC (min): 26.6 min. M (FD): m/z (%) = 359.1 (100); 360.1 (17.4); calc.[C22H17NO4] = 359.1

Reference： [1]Tetrahedron Letters,2013,vol. 54,p. 753 - 756
[2]Chemical Communications,2013,vol. 49,p. 4555 - 4557
[3]Journal of Chemical Research, Miniprint,1998,p. 2736 - 2753
[4]Chemical Communications,2014,vol. 50,p. 1691 - 1693

7
[ 185116-43-2 ]
WangBromo resin [ No CAS ]
Wang resin-OC(O)-C₆H₄-NH₂(p) [ No CAS ]

Reference： [1]Tetrahedron,2002,vol. 58,p. 5147 - 5158

8
[ 156-38-7 ]
[ 100-39-0 ]
[ 7693-46-1 ]
[ 185116-43-2 ]
[ 106-89-8 ]
4-{2-[4-(3-benzyl-2-oxo-oxazolidin-5-ylmethoxy)-phenyl]-acetylamino}-benzamide [ No CAS ]

Reference： [1]Tetrahedron Letters,2002,vol. 43,p. 8327 - 8330

9
[ 100-39-0 ]
[ 7693-46-1 ]
[ 185116-43-2 ]
[ 106-89-8 ]
[ 99-96-7 ]
C₂₅H₂₃N₃O₅ [ No CAS ]

Reference： [1]Tetrahedron Letters,2002,vol. 43,p. 8327 - 8330

10
[ 156-38-7 ]
[ 7693-46-1 ]
[ 70-11-1 ]
[ 185116-43-2 ]
[ 106-89-8 ]
4-(2-{4-[2-oxo-3-(2-oxo-2-phenyl-ethyl)-oxazolidin-5-ylmethoxy]-phenyl}-acetylamino)-benzamide [ No CAS ]

Reference： [1]Tetrahedron Letters,2002,vol. 43,p. 8327 - 8330

11
[ 7693-46-1 ]
[ 70-11-1 ]
[ 185116-43-2 ]
[ 106-89-8 ]
[ 99-96-7 ]
C₂₆H₂₃N₃O₆ [ No CAS ]

Reference： [1]Tetrahedron Letters,2002,vol. 43,p. 8327 - 8330

12
[ 100-09-4 ]
[ 185116-43-2 ]
4-(4-methoxybenzoylamino)benzohydroxamic acid [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry,2004,vol. 12,p. 37 - 44

13
[ 505-73-7 ]
[ 56583-58-5 ]
[ 185116-43-2 ]
TGGTGCGAA-Lys(Boc)-Lys(Boc)-NH₂ [ No CAS ]
H₂N-CH(2napAla)-CO-S-CH₂CONH-pC₆H₄-CO-Gly₂-TGGTGCGAA-Lys₂-NH₂ [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2004,vol. 126,p. 15984 - 15989

14
[ 505-73-7 ]
[ 55516-54-6 ]
[ 185116-43-2 ]
TGGTGCGAA-Lys(Boc)-Lys(Boc)-NH₂ [ No CAS ]
H₂N-CH(1napAla)-CO-S-CH₂CONH-pC₆H₄-CO-Gly₂-TGGTGCGAA-Lys₂-NH₂ [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2004,vol. 126,p. 15984 - 15989

15
[ 505-73-7 ]
[ 185116-43-2 ]
N-pentenoyl-L-2-anthrylalanine [ No CAS ]
TGGTGCGAA-Lys(Boc)-Lys(Boc)-NH₂ [ No CAS ]
H₂N-CH(Pen-2antAla)-CO-S-CH₂CONH-pC₆H₄-CO-Gly₂-TGGTGCGAA-Lys₂-NH₂ [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2004,vol. 126,p. 15984 - 15989

16
[ 688763-60-2 ]
[ 505-54-4 ]
[ 71989-23-6 ]
[ 185116-43-2 ]
(S)-2-((S)-3-Carbamoyl-2-{15-[(1S,2S)-1-(4-carbamoyl-phenylcarbamoyl)-2-methyl-butylcarbamoyl]-pentadecanoylamino}-propionylamino)-3-phenyl-propionic acid [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2005,vol. 48,p. 2239 - 2242

17
[ 104004-96-8 ]
[ 185116-43-2 ]
XCH₂-COOH [ No CAS ]
4-(2-[4-((8S,11R,13S,14S,17S)-17-Hydroxy-13-methyl-3-oxo-17-prop-1-ynyl-2,3,6,7,8,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-11-yl)-phenyl]-methyl-amino}-acetylamino)-benzoic acid [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 40 - 44

18
[ 185116-43-2 ]
[ 52407-60-0 ]

Reference： [1]Journal of Chemical Research, Miniprint,1998,p. 2736 - 2753

19
[ 185116-43-2 ]
[ 218603-30-6 ]

Reference： [1]Journal of Chemical Research, Miniprint,1998,p. 2736 - 2753

20
[ 185116-43-2 ]
N-<4-<N-(6-<<(aminocarbonyl)amino>carbonyl>pyridin-2-ylmethyl)>aminobenzoyl>-L-glutamic acid [ No CAS ]

Reference： [1]Journal of Chemical Research, Miniprint,1998,p. 2736 - 2753

21
[ 185116-43-2 ]
[ 218603-08-8 ]

Reference： [1]Journal of Chemical Research, Miniprint,1998,p. 2736 - 2753

22
polyethylene glycol polyamide resin [ No CAS ]
[ 185116-43-2 ]
C₇H₇N₂OPol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		To a mixture of Rink amine resin (503 mg, 0.10 mmol) in DMF (4 mL) was added N-Fmoc-4-aminobenzoic acid (111 mg, 0.30 mmol), DIC (N,N'-diisopropylcarbodiimide) (48 muL, 0.30 mmol), and HOBT (1-hydroxybenzo-triazole) (41 mg, 0.30 mmol). The mixture was stirred at room temperature overnight under argon. The resin was filtered off and washed repeated with DMF, MeOH and DCM. The resin was then treated with 20% piperidine in DMF for half an hour, filtered off and washed repeatly with DMF, MeOH and DCM, dried under vacuum.

Reference： [1]Patent: US2004/10162,2004,A1 .Location in patent: Page 17

23
N-9-fluorenylmethyloxycarbonyl-4-benzoyl-D-phenylalanine [ No CAS ]
[ 53293-00-8 ]
[ 185116-43-2 ]
[ 1011719-40-6 ]

Reference： [1]Journal of the American Chemical Society,2008,vol. 130,p. 2184 - 2194

24
N-9-fluorenylmethyloxycarbonyl-4-benzoyl-D-phenylalanine [ No CAS ]
[ 53293-00-8 ]
[ 185116-43-2 ]
C₂₉H₂₆N₂O₅ [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2008,vol. 130,p. 2184 - 2194

25
[ 53293-00-8 ]
[ 88574-06-5 ]
2-([(9H-fluoren-9-yl)methoxy]carbonyl}amino)-3-(4-benzoylphenyl)propanoic acid [ No CAS ]
[ 185116-43-2 ]
[ 1011719-43-9 ]

Reference： [1]Journal of the American Chemical Society,2008,vol. 130,p. 2184 - 2194

26
[ 53293-00-8 ]
[ 149834-58-2 ]
2-([(9H-fluoren-9-yl)methoxy]carbonyl}amino)-3-(4-benzoylphenyl)propanoic acid [ No CAS ]
[ 185116-43-2 ]
methyl-8-chloro-8-oxooctanoate [ No CAS ]
C₄₄H₅₄N₄O₇ [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2008,vol. 130,p. 2184 - 2194

27
[ 53293-00-8 ]
2-([(9H-fluoren-9-yl)methoxy]carbonyl}amino)-3-(4-benzoylphenyl)propanoic acid [ No CAS ]
[ 185116-43-2 ]
[ 1011719-39-3 ]

Reference： [1]Journal of the American Chemical Society,2008,vol. 130,p. 2184 - 2194

28
[ 53293-00-8 ]
2-([(9H-fluoren-9-yl)methoxy]carbonyl}amino)-3-(4-benzoylphenyl)propanoic acid [ No CAS ]
[ 185116-43-2 ]
C₂₉H₂₆N₂O₅ [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2008,vol. 130,p. 2184 - 2194

29
[ 41624-92-4 ]
[ 102169-54-0 ]
2-([(9H-fluoren-9-yl)methoxy]carbonyl}amino)-3-(4-benzoylphenyl)propanoic acid [ No CAS ]
[ 185116-43-2 ]
C₃₈H₄₃N₃O₆ [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2008,vol. 130,p. 2184 - 2194

30
[ 771-61-9 ]
[ 185116-43-2 ]
[ 1031755-95-9 ]

Reference： [1]European Journal of Organic Chemistry,2008,p. 1582 - 1588

31
[ 82911-69-1 ]
[ 150-13-0 ]
[ 185116-43-2 ]

Reference： [1]European Journal of Organic Chemistry,2008,p. 1582 - 1588
[2]Biological Chemistry,2015,vol. 396,p. 45 - 52

32
4-O-methylhydroxylaminephenoxymethyl-copoly(styrene-1%-divinylbenzene)-resin [ No CAS ]
[ 185116-43-2 ]
C₂₂H₁₇N₂O₄Pol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		Step A A mixture of HOAt (55 mg, 0.4 mmoles) and HATU (152 mg, 0.4 mmoles) in anhydrous DMF (0.5 ml), followed by diisopropyl ethylamine (0.14 ml, 0.8 mmoles), was added to a solution of 4- (9H-FLUOREN-9-YL- METHOXYCARBONYLAMINO)- benzoic acid (150. mg, 0.4 MMOLES) IN anhydrous DMF (0.5 ml). The reaction mixture was stirred at ambient temperature for 30 minutes and was then transferred into a reactor containing a Wang type polystyrene resin, functionalized with hydroxylamine (0.1 g; 0.1 mmoles), and the suspension was stirred at ambient temperature for 16 hours. The resin was filtered and washed, in sequence, with DMF (5x2 ml), DCM (2x2 ml), MEOH (2x2 ML), DCM (2x2 ml), MeoH (2x2 ml), DCM (2x2 ml) and DMF (5x2 ml); finally, the resin was filtered and dried under vacuum.

Reference： [1]Patent: WO2004/63146,2004,A1 .Location in patent: Page 9-10

33
[ 65-85-0 ]
[ 185116-43-2 ]
N-[(9-fluorenyl)methoxycarbonyl]-3-(2-naphthyl)-D-alanine [ No CAS ]
[ 873113-34-9 ]

Yield	Reaction Conditions	Operation in experiment
		A mixture of HOAt (5.1 g; 37.5 mmol) and HATU (14.3 g; 37.5 mmol) inanhydrous DMF (20 ml) was added to a solution of 4-(9H-fluoren-9-yl-methoxycarbonylamino)-benzoic acid (13.5 g; 37.5 mmol) in anhydrousDMF (25 ml) and diisopropylethylamine (13 ml; 75 mmol) was thenadded. The reaction mixture was stirred at ambient temperature for 30minutes, then was transferred into a reactor containing a Wang typepolystyrene resin functionalised with hydroxylamine (9 g; 9.36 mmol) andthe suspension was stirred at ambient temperature for 16 hours. The resinwas filtered out and washed, hi succession, with DMF (5x50 ml), DCM(4x50 ml), MeOH (3x50 ml) and DCM (5x50 ml), was finally filtered outand dried under a vacuum.StepBAn aliquot of the resin obtained in A (150 mg) was transferred into a solidphase synthesis reactor and reswollen with a 20% solution of piperidine inDMF (2 ml). After having been stirred at ambient temperature for one hour,the resin was filtered out and washed with DMF (5x2 ml).StepCHATU (237 mg, 0.62 mmol), HOAt (85 mg; 0.62 mmol) and DIPEA(0.217 ml; 1.24 mmol) were added to a solution of (9H-fluoren-9-yl)-methoxycarbonyl-D-(2)naphthylalanine (Fmoc-D(2)Nal-OH; 273 mg, 0.62mmol) in DMF (1.5 ml). The solution (~2 ml) was added to the reactorcontaining the resin obtained in B and stirred overnight at ambienttemperature. The resin was filtered out and washed, in succession, withDMF (5x2 ml), DCM (2x2 ml), MeOH (2x2 ml), DCM (2x2 ml) and finallyfiltered out under a vacuum.StepDThe resin obtained in C was treated with 20% piperidine in DMF, asdescribed in step B.StepEHATU (237 mg, 0.62 mmol), HOAt (85 mg; 0.62 mmol) and DIPEA(0.217 ml; 1.24 mmol) were added to a solution of benzoic acid (76 mg;0.62 mmol) in DMF (1.5 ml). The solution (~2 ml) was added to the reactorcontaining the resin obtained in D and stirred overnight at ambienttemperature. The resin was filtered out and washed, in succession, withDMF (5x2 ml), DCM (2x2 ml), MeOH (2x2 ml), DCM (2x2 ml) and finallyfiltered out under a vacuum.StepFThe resin obtained as described in the preceding point was reswollen in a50% solution of TFA in DCM (2 ml) and stirred at ambient temperature forone hour, then was filtered out and the solution was evaporated to dryness.The residue was resuspended with t-BuOMe and evaporated five moretimes. The residue obtained was purified by means of preparativeHPLC/MS in accordance with the previously described general method.Product obtained: 16.9 mg; [M+H+ = 454.3 (calc. 454.2)

Reference： [1]Patent: WO2006/3068,2006,A2 .Location in patent: Page/Page column 11-13

34
[ 3326-32-7 ]
[ 29022-11-5 ]
[ 35661-60-0 ]
[ 132327-80-1 ]
[ 111061-56-4 ]
[ 185116-43-2 ]
(S)-2-(((9H-fluoren-9-yl)methoxy)carbonylamino)-3-(4(bis(dimethylamino)phosphoryloxy)phenyl)propanoic acid [ No CAS ]
[ 1133164-54-1 ]

Reference： [1]Journal of Medicinal Chemistry,2009,vol. 52,p. 1612 - 1618

35
C₃₈H₄₃N₂O₇PolS [ No CAS ]
[ 29022-11-5 ]
[ 35661-40-6 ]
[ 185116-43-2 ]
C₄₁H₅₀N₅O₈PolS [ No CAS ]

Reference： [1]Molecules,2010,vol. 15,p. 1590 - 1631

36
C₃₈H₄₃N₂O₇PolS [ No CAS ]
[ 29022-11-5 ]
[ 95753-55-2 ]
[ 185116-43-2 ]
C₄₁H₄₉N₆O₁₀PolS [ No CAS ]

Reference： [1]Molecules,2010,vol. 15,p. 1590 - 1631

37
C₃₈H₄₃N₂O₇PolS [ No CAS ]
[ 29022-11-5 ]
[ 185116-43-2 ]
C₃₄H₄₄N₅O₈PolS [ No CAS ]

Reference： [1]Molecules,2010,vol. 15,p. 1590 - 1631

38
C₁₆H₂₇N₄O₄PolS [ No CAS ]
[ 185116-43-2 ]
C₃₈H₄₂N₅O₇PolS [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2010,vol. 53,p. 432 - 440

39
[ 25952-53-8 ]
[ 185116-43-2 ]
C₃₀H₃₄N₄O₄*ClH [ No CAS ]

Reference： [1]Organic and Biomolecular Chemistry,2010,vol. 8,p. 835 - 840

40
[ 21169-71-1 ]
[ 71989-23-6 ]
[ 7144-05-0 ]
[ 135673-97-1 ]
[ 185116-43-2 ]
[ 1252806-72-6 ]

Reference： [1]Journal of Medicinal Chemistry,2010,vol. 53,p. 7428 - 7440

41
C₉₀H₁₀₆N₉O₁₅PolS [ No CAS ]
[ 185116-43-2 ]
[ 1268717-49-2 ]

Reference： [1]Journal of Medicinal Chemistry,2011,vol. 54,p. 1308 - 1313

42
[ 185116-43-2 ]
[ 1363453-85-3 ]

Reference： [1]Journal of Medicinal Chemistry,2012,vol. 55,p. 3319 - 3330

43
[ 185116-43-2 ]
[ 1363454-26-5 ]

Reference： [1]Journal of Medicinal Chemistry,2012,vol. 55,p. 3319 - 3330

44
[ 185116-43-2 ]
[ 1363454-28-7 ]

Reference： [1]Journal of Medicinal Chemistry,2012,vol. 55,p. 3319 - 3330

45
[ 185116-43-2 ]
[ 1363454-31-2 ]

Reference： [1]Journal of Medicinal Chemistry,2012,vol. 55,p. 3319 - 3330
[2]Patent: WO2013/36749,2013,A1

46
[ 185116-43-2 ]
[ 1363454-33-4 ]

Reference： [1]Journal of Medicinal Chemistry,2012,vol. 55,p. 3319 - 3330
[2]Patent: WO2013/36749,2013,A1

47
[ 185116-43-2 ]
[ 1071005-70-3 ]

Yield	Reaction Conditions	Operation in experiment
	With 1-methyl-pyrrolidin-2-one; thionyl chloride; at 20℃; for 2h;	General procedure: The respective carboxylic acid(4 or N-Fmoc-p-aminobenzoic acid) was dissolved in thionyl chloride and a catalytic amount of dry NMP was added. After stirring for 2hrs at rt, thionylchloride was removed under reduced pressure.The acid chloride was dissolved in dry NMP (to obtain a final concentration of 0.5mmol/ml) and the solution filtered through a 400 micron syringe filter into the cartridges of the peptide synthesizer (1mmol percartridge).
	With thionyl chloride; for 2h;Reflux;	00132] 2- (4-(( ( (9H-fluoren-9-yl)methoxy) carbonyl) amino)phenyl) benzo [d] thiazole-6-carboxylic acid (39). To a suspension of zinc salt 37 (Wu et al . (2007) Bioorg. Med. Chem. 15:2789-2796) (266 mg, 0.66 mmol) in pyridine (5 mL) at 80C, was added (9ff-fluoren-9-yl) methyl (4- ( chlorocarbonyl) phenyl) carbamate (500 mg, 1.32 mmol), which was prepared from 4- ( ( ( ( 9ff-fluoren-9- yl) methoxy) carbonyl) amino) benzoic acid refluxed with S0C12 for 2 hours. The reaction mixture was stirred at 80C for 16 hours. The resulting residue after evaporation was purified by reverse phase HPLC. Yield: 196 mg, 30%. ½ NMR (400 MHz, DMSO) 510.15 (s, 1H) , 8.74 (s, 1H) , 8.07 - 8.05 (m, 4H) , 7.93 (d, J = 7.5 Hz, 2H) , 7.78 (d, J = 7.5 Hz, 2H) , 7.69 (s, br. 2H) , 7.45 (t, J = 7.3 Hz, 2H) , 7.37 (t, J = 7.3 Hz, 2H) , 4.56 (d, J = 6.5 Hz, 2H) , 4.36 (d, J = 6.5 Hz, 1H) . 13C NMR (101 MHz, DMSO) delta 170.5, 166.9, 156.4, 153.2, 143.7, 142.5, 140.8, 134.4, 128.4, 127.7, 127.5, 127.4, 127.1, 126.6, 125.1, 124.2, 122.2, 120.2, 118.4, 65.8, 46.6. HRMS (m/z) : calcd for C29H21N2O S (neutral M+H) 493.1222; found 493.1221.

Reference： [1]Journal of Medicinal Chemistry,2012,vol. 55,p. 3319 - 3330
[2]Journal of Medicinal Chemistry,2012,vol. 55,p. 3170 - 3181
[3]Tetrahedron Letters,2013,vol. 54,p. 753 - 756
[4]Patent: WO2013/36749,2013,A1 .Location in patent: Paragraph 00132

48
[ 185116-43-2 ]
[ 1363453-59-1 ]

Reference： [1]Journal of Medicinal Chemistry,2012,vol. 55,p. 3319 - 3330

49
[ 185116-43-2 ]
[ 905111-57-1 ]

Reference： [1]Journal of Medicinal Chemistry,2012,vol. 55,p. 3170 - 3181

50
[ 185116-43-2 ]
[ 1352126-58-9 ]

Reference： [1]Journal of Medicinal Chemistry,2012,vol. 55,p. 3170 - 3181

51
[ 185116-43-2 ]
[ 1018244-82-0 ]

Reference： [1]Journal of Medicinal Chemistry,2012,vol. 55,p. 3170 - 3181

52
[ 185116-43-2 ]
[ 909504-54-7 ]

Reference： [1]Journal of Medicinal Chemistry,2012,vol. 55,p. 3170 - 3181

53
N-Fmoc-L-Pro Wang resin [ No CAS ]
[ 619-65-8 ]
[ 185116-43-2 ]
[ 1378484-09-3 ]

Yield	Reaction Conditions	Operation in experiment
79%		General procedure for the synthesis of test compounds by solid phase peptide synthesis (SPPS); All the compounds were synthesized using Fmoc based solid-phase peptide synthesis protocol. Rink amide MBHA resin preloaded with Fmoc-Proline (750 mg, 0.58 mmol/g) was swollen in DMF for 20 min and washed with DMF (3 X 25 ml). Fmoc group of the resin bound Proline was removed by agitating peptidyl resin in 20% piperidine solution (25 ml, 1 X 5 min and 1 X 30 min) for the next coupling reaction. Fmoc--Ala-OH/ Fmoc-GABA-OH/ <strong>[185116-43-2]Fmoc-PABA-OH</strong> were coupled to the peptidyl resin by agitating their respective preactivated solutions under N2 atmosphere. (i.e. Fmoc-XX-OH (4 equiv), HOBt (4 equiv), and DIC (4 equiv) in DMF (5 mL) for 30 min.). After completion of the coupling reaction confirmed by Kaiser ninhydrin and TNBS tests, peptidyl resin was washed with DMF, DCM and ether (3 X 25 ml each) and treated with 20% piperidine solution (25 ml, 1 X 5 min and 1 X 30 min) to remove Fmoc group. Peptidyl resin was then washed with DMF, DCM and ether (3 X 25 ml each) and swollen in DMF for 30 min for the coupling of benzoic acids. Substituted benzoic acids were incorporated to the respective peptidyl resin by agitating peptidyl rasine in the preactivated coupling solution of respective benzoic acid under N2 atm. over a period of 2-4hrs. Completion of coupling was confirmed by Kaiser ninhydrin and TNBS tests, whenever coupling was found incomplete one more coupling cycle was performed. Then, the resin was washed with DMF, DCM and ether (5 X 25ml each) and dried under vacuum for the global cleavage to get the desired peptidomimetics. Cleavage; The desired peptidomimetics were cleaved and deprotected from their respective peptidyl-resins by treatment with TFA cleavage mixture as follows. A solution of TFA / Water / Triisopropylsilane (95: 2.5: 2.5) (10 ml / 100 mg of peptidyl-resin) was added to peptidyl-resins and the mixture was kept at room temperature with occasional starring. The resin was filtered, washed with a cleavage mixture and the combined filtrate was evaporated to dryness. Residue obtained was triturated with ether (20 ml each) to yield crude compounds, typically in >100% yield (Ca 200-230 mg). Crude compounds thus obtained were purified by preparative HPLC as follows: Purification; Preparative HPLC was carried out on a Shimadzu LC-8A liquid chromatograph. A solution of crude compounds dissolved in water: ACN (1:1, 5ml) or Methanol (5ml) was injected into a semi-Prep column (Luna 10 mu; C18; 210-220 nm), dimension 250 X 21.20 mm and eluted with a linear gradient of ACN in water, both buffered with 0.1 % TFA, using a flow rate of 15 ml / min, with effluent monitoring by PDA detector at 220 nm. A typical gradient of 20 % to 70 % of water-ACN mixture, buffered with 0.1 % TFA was used, over a period of 100 minutes, with 1% gradient change per minute. The desired product eluted were collected in a single 50-80 ml fraction and pure peptidomimetics were obtained as white solids either by lyophilisation of respective HPLC fractions or by normal work up procedure after evaporation of ACN from the fractions and extraction with DCM.