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Quality Control of [ 117322-30-2 ]

COA NMR CNMR HPLC LC-MS

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Product Details of [ 117322-30-2 ]

CAS No. :	117322-30-2	MDL No. :	MFCD01074696
Formula :	C₂₁H₂₁NO₄	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	IECZEINPZOFWNU-UHFFFAOYSA-N
M.W :	351.40	Pubchem ID :	978345
Synonyms :

Safety of [ 117322-30-2 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 117322-30-2 ]

* 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 [ 117322-30-2 ]
Downstream synthetic route of [ 117322-30-2 ]

[ 117322-30-2 ] Synthesis Path-Upstream 1~3

1
[ 82911-69-1 ]
[ 52-52-8 ]
[ 117322-30-2 ]

Yield	Reaction Conditions	Operation in experiment
28%	Stage #1: With sodium hydrogencarbonate In water; acetonitrile at 20℃; Stage #2: With hydrogenchloride In water; acetonitrile	1- (((9H-Fluoren-9-yl)methoxy)carbonylamino)cyclopentanecarboxylic acid(compound 4 of example A): Fmoc-OSu (3.13 g, 9.3 mmol) was added to a solution of 1- aminocyclo- pentanecarboxylic acid (1.0 g, 7.8 mmol) and NaHC0₃ (1.63 g, 19.4 mmol) in acetonitrile/water (100 mL, 1 : 1). The reaction mixture was stirred at room temperature overnight. Most of the solvent was removed under reduced pressure and the resulting mixture was adjusted to pH = 2 with 2 N HCI and extracted with DCM. The combined extracts were washed with brine, dried over anhydrous Na₂S0₄ and concentrated. The residue was purified by flash column chromatography on silica gel (PE/EA = 20: 1) to afford compound 4 of example A (0.75 g, 28percent yield) as a white solid.

Reference： [1] Journal of the American Chemical Society, 2000, vol. 122, # 37, p. 8898 - 8909
[2] Patent: WO2012/119941, 2012, A1, . Location in patent: Page/Page column 110
[3] Journal of the American Chemical Society, 2003, vol. 125, # 23, p. 6852 - 6853
[4] Bioorganic and Medicinal Chemistry, 2013, vol. 21, # 18, p. 5694 - 5706

2
[ 497-19-8 ]
[ 52-52-8 ]
[ 117322-30-2 ]

Reference： [1] Patent: US5385910, 1995, A,

3
[ 28920-43-6 ]
[ 52-52-8 ]
[ 117322-30-2 ]

Reference： [1] Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, 2001, vol. 40, # 1, p. 70 - 74

[ 117322-30-2 ] Synthesis Path-Downstream 1~59

1
[ 117322-30-2 ]
[ 133690-73-0 ]
[ 151257-02-2 ]

Reference： [1]Journal of Medicinal Chemistry,1993,vol. 36,p. 3371 - 3380

2
[ 28920-43-6 ]
[ 52-52-8 ]
[ 117322-30-2 ]

Reference： [1]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,2001,vol. 40,p. 70 - 74

3
[ 82911-69-1 ]
[ 52-52-8 ]
[ 117322-30-2 ]

Yield	Reaction Conditions	Operation in experiment
28%		1- (((9H-Fluoren-9-yl)methoxy)carbonylamino)cyclopentanecarboxylic acid(compound 4 of example A): Fmoc-OSu (3.13 g, 9.3 mmol) was added to a solution of 1- aminocyclo- pentanecarboxylic acid (1.0 g, 7.8 mmol) and NaHC03 (1.63 g, 19.4 mmol) in acetonitrile/water (100 mL, 1 : 1). The reaction mixture was stirred at room temperature overnight. Most of the solvent was removed under reduced pressure and the resulting mixture was adjusted to pH = 2 with 2 N HCI and extracted with DCM. The combined extracts were washed with brine, dried over anhydrous Na2S04 and concentrated. The residue was purified by flash column chromatography on silica gel (PE/EA = 20: 1) to afford compound 4 of example A (0.75 g, 28% yield) as a white solid.
	With sodium carbonate; In tetrahydrofuran; water; at 20℃; for 18h;pH 8 - 9;	General procedure: To 250 mL round-bottomed flask add 1a or 1c or 1g or 1h, 2.5 equiv Fmoc-OSu, 50 mL THF/H2O (1:1, v/v), pH of the solution was adjusted with saturated sodium carbonate to 8-9, and the reaction continued at room temperature for about 18h. After that, the solution was extracted twice with ether, and pH of aqueous layer was adjusted with concentrated HCl to 5, white precipitation was obtain and dried in vacuum to gave corresponding product (2a or 2c or 2g or 2h).

Reference： [1]Journal of the American Chemical Society,2000,vol. 122,p. 8898 - 8909
[2]Patent: WO2012/119941,2012,A1 .Location in patent: Page/Page column 110
[3]Journal of the American Chemical Society,2003,vol. 125,p. 6852 - 6853
[4]Bioorganic and Medicinal Chemistry,2013,vol. 21,p. 5694 - 5706

4
[ 6940-78-9 ]
[ 28920-43-6 ]
Wang resin-OC(O)CH₂N=CPh₂ [ No CAS ]
[ 117322-30-2 ]

Reference： [1]Tetrahedron Letters,2003,vol. 44,p. 8403 - 8406

5
[ 771-61-9 ]
[ 117322-30-2 ]
[ 309920-58-9 ]

Reference： [1]Journal of the American Chemical Society,2000,vol. 122,p. 8898 - 8909

6
[ 6314-28-9 ]
[ 929-59-9 ]
[ 35661-40-6 ]
[ 117322-30-2 ]
C₃₀H₃₈N₄O₅S [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 4841 - 4844

7
[ 123-00-2 ]
[ 6314-28-9 ]
[ 86123-10-6 ]
[ 117322-30-2 ]
MEN 14268 [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 4841 - 4844

8
[ 4572-03-6 ]
[ 6314-28-9 ]
[ 86123-10-6 ]
[ 117322-30-2 ]
C₃₂H₄₁N₅O₃S [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 4841 - 4844

9
[ 117322-30-2 ]
3-[7-(2-[1-(9H-fluoren-9-ylmethoxycarbonylamino)-cyclopentanecarbonyl]-amino}-ethyl)-1,3,6,8-tetraoxo-3,6,7,8-tetrahydro-1H-benzo[lmn][3,8]phenanthrolin-2-yl]-propionic acid [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2000,vol. 122,p. 8898 - 8909

10
[ 117322-30-2 ]
[ 138402-04-7 ]

Reference： [1]Journal of Medicinal Chemistry,1993,vol. 36,p. 3371 - 3380

11
[ 117322-30-2 ]
[ 138401-20-4 ]

Reference： [1]Journal of Medicinal Chemistry,1993,vol. 36,p. 3371 - 3380

12
[ 117322-30-2 ]
[ 138401-34-0 ]

Reference： [1]Journal of Medicinal Chemistry,1993,vol. 36,p. 3371 - 3380

13
[ 117322-30-2 ]
[ 151257-08-8 ]

Reference： [1]Journal of Medicinal Chemistry,1993,vol. 36,p. 3371 - 3380

14
[ 117322-30-2 ]
SR 47155A [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,1993,vol. 36,p. 3371 - 3380

15
[ 117322-30-2 ]
4'-<(2-n-butyl-4-oxo-1,3-diazaspiro<4.4>nonan-3-yl)methyl>biphenyl-2-carboxylic acid trifluoroacetate [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,1993,vol. 36,p. 3371 - 3380

16
[ 117322-30-2 ]
tert-butyl-4'-<(2-n-butyl-4-thioxo-1,3-diazaspiro<4.4>non-1-en-3-yl)methyl>biphenyl-2-carboxylic acid trifluoroacetate [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,1993,vol. 36,p. 3371 - 3380

17
[ 110-89-4 ]
rapamycin 42-ester [ No CAS ]
[ 117322-30-2 ]
[ 53123-88-9 ]

Yield	Reaction Conditions	Operation in experiment
0.36 g (0.35 mmole, 44%)	In methanol; acetonitrile;	EXAMPLE 10 Rapamycin 42-ester with 1-aminocyclopentane carboxylic acid To a chilled (ice bath) solution of rapamycin 42-ester with 1-(9H-fluoren-9-ylmethoxycarbonylamino)-cyclopentane carboxylic acid (0.991 g, 0.794 mmol) in acetonitrile (4.5 mL) was added 0.47 mL (4.76 mmol) of piperidine in 2 mL of acetonitrile via an additional funnel. The reaction mixture was stirred at 0-5 C. for about two hours (a white precipitate formed after an hour). The reaction mixture was then filtered and concentrated (without heating) and applied to a flash column with a gradient of 1-1.5% methanol/chloroform to yield 0.36 g (0.35 mmole, 44%) of the title compound. Negative FAB-MS [M-H]- am/z 1024.

Reference： [1]Patent: US5385910,1995,A

18
fluorenylmethyloxycarbonyl chloride [ No CAS ]
[ 497-19-8 ]
[ 52-52-8 ]
[ 117322-30-2 ]

Yield	Reaction Conditions	Operation in experiment
16.6%	In 1,4-dioxane; alumina-filtered dioxane;	EXAMPLE 8 1-(9H-Fluoren-9-ylmethoxycarbonylamino)-cyclopentane carboxylic acid To a chilled (ice bath) suspension of aminocyclopentanecarboxylic acid (1.05 g, 8.13 mmol) in alumina-filtered dioxane (8 mL) was added 10% Na2 CO3 (16.5 mL). The reaction mixture became clearer (but not completely clear) after 10% Na2 CO3 was added. A solution of a fluorenylmethyl chloroformate (2.11 g, 8.16 mmol in 12 mL dioxane) was then slowly added to the reaction mixture, which became (and remained) cloudy. The reaction mixture was allowed to warm to room temperature (~20 C.) and was stirred overnight under N2. The reaction mixture was poured into ice water (~150 mL) and extracted three times with anhydrous ether. (Some product went into the ether layer). The aqueous layer was chilled in an ice bath, acidified with concentrated HCl to pH of about 2, and extracted three times with ethyl acetate (3*50 mL). The combined ethyl acetate layers were washed with 0.1N HCl and H2 O. The ether and ethyl acetate layers were dried over MgSO4, combined and concentrated. Flash chromatography (40-50% ethyl acetate/hexane) gave the title compound as a white foam in a yield of 16.6% (0.476 g (1.35 mmol). DEI m+am/z 351.

Reference： [1]Patent: US5385910,1995,A

19
[ 117322-30-2 ]
(9H-fluoren-9-yl)methyl [1-(fluorocarbonyl)cyclopentyl]carbamate [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2018,vol. 140,p. 3690 - 3711
[2]Journal of the American Chemical Society,2008,vol. 130,p. 14382 - 14383

20
[ 117322-30-2 ]
[ 18107-18-1 ]
C₂₂H₂₃NO₄ [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2009,vol. 19,p. 976 - 980

21
[ 35661-60-0 ]
[ 35661-39-3 ]
[ 71989-23-6 ]
[ 71989-26-9 ]
[ 71989-35-0 ]
[ 71989-28-1 ]
[ 132388-59-1 ]
[ 132327-80-1 ]
[ 117322-30-2 ]
[ 143824-78-6 ]
Nα-(9-fluorenylmethyloxycarbonyl)-Nγ-2,2,4,6,7-pentamethyldihydrobenzofuran-5-sulfonyl-L-arginine [ No CAS ]
H-(1-amino-1-cyclopentyl-carboxyl)-QGTFTSDYSKYLDSRRAQDFVQWLMNTKRNRNNIA-NH₂ [ No CAS ]

Reference： [1]Journal of Peptide Science,2011,vol. 17,p. 270 - 280

22
[ 67-56-1 ]
C₂₄H₂₀NO₄Pol [ No CAS ]
[ 200871-52-9 ]
[ 71989-31-6 ]
[ 117322-30-2 ]
Fmoc-D-Tyr(O-tBu)-OH [ No CAS ]
C₄₆H₆₃N₇O₉ [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2012,vol. 134,p. 9755 - 9761

23
[ 1398718-28-9 ]
[ 117322-30-2 ]
[ 1398718-52-9 ]

Yield	Reaction Conditions	Operation in experiment
56%		(S)-(9H-Fluoren-9-yl)methyl l-(l-cyano-2-(4'-((4-methylpiperazin-l-yl)methyl) biphenyl-4-yl)ethylcarbamoyl)cyclopentylcarbamate (Fmoc-PZ1044)DMTMM (663 mg, 2.4 mmol) was added to a solution of compound PZ1024-6 from example 1 (400 mg, 1.2 mmol) in DCM (25.0 mL) in an ice-water bath. The mixture was stirred at 0C for 0.5 h and compound 4 from example A described in the MATERIALS AND METHODS section (444 mg, 1.32 mol) was added. The reaction mixture was allowed to warm to room temperature and stirred for 12 h. Water was added and the resulting mixture was extracted with DCM. The combined extracts were washed with brine, dried over anhydrous Na2S04 and concentrated. The residue was purified by flash column chromatography on silica gel (PE/EA = 1 : 1 then EA/MeOH = 40 : 1) to afford compound Fmoc-PZ1044 (452 mg, 56% yield) as a white solid.

Reference： [1]Patent: WO2012/119941,2012,A1 .Location in patent: Page/Page column 125

24
[ 1398718-28-9 ]
[ 117322-30-2 ]
[ 1398717-89-9 ]

Reference： [1]Patent: WO2012/119941,2012,A1

25
[ 1421263-51-5 ]
[ 117322-30-2 ]
(S)-2-amino-5-(3-(2,2,4,6,7-pentamethyl-2,3-dihydrobenzofuran-5-ylsulfonyl)guanidino)pentanoic acid [ No CAS ]
[ 1417329-23-7 ]

Reference： [1]Journal of the American Chemical Society,2013,vol. 135,p. 669 - 682

26
[ 117322-30-2 ]
C₃₅H₅₁N₇O₄*C₂HF₃O₂ [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2013,vol. 135,p. 669 - 682

27
[ 117322-30-2 ]
C₃₅H₄₉F₂N₇O₄*C₂HF₃O₂ [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2013,vol. 135,p. 669 - 682

28
[ 117322-30-2 ]
C₃₅H₄₉Cl₂N₇O₄*C₂HF₃O₂ [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2013,vol. 135,p. 669 - 682

29
[ 36321-43-4 ]
[ 117322-30-2 ]
[ 1453814-86-2 ]

Yield	Reaction Conditions	Operation in experiment
	With benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine; diisopropyl-carbodiimide; In tetrahydrofuran; at 20℃; for 18h;	General procedure: To a 100 mL round-bottomed flask add equimolar 2a and 2b, 1.2 equiv 1-hydroxybenzotriazole (HOBt), 1.2 equiv DIC, 2.5 equiv N,N-diisopropylethylamine (DIEA), the mixture was stirred in about 30mL dry THF at room temperature for 18h. The solvents were removed in vacuo to give white solid 3a, without further purification, 3a was subjected to 16mL DMF and 4mL piperidine for 30min. The product was added 100 mL deionized water, and extracted twince with 20mL CH2Cl2, dried over anhydrous sodium sulfate. The solvents were removed in vacuo, flash chromatography of the residue on silica gel (CH2Cl2/CH3OH=8:1, v/v) gave pure product 4a. Compounds 4b-4g were prepared with the same procedure.

Reference： [1]Bioorganic and Medicinal Chemistry,2013,vol. 21,p. 5694 - 5706

30
[ 117322-30-2 ]
[ 1453814-88-4 ]

Reference： [1]Bioorganic and Medicinal Chemistry,2013,vol. 21,p. 5694 - 5706

31
[ 117322-30-2 ]
[ 1453814-90-8 ]

Reference： [1]Bioorganic and Medicinal Chemistry,2013,vol. 21,p. 5694 - 5706

32
[ 117322-30-2 ]
[ 1453814-92-0 ]

Reference： [1]Bioorganic and Medicinal Chemistry,2013,vol. 21,p. 5694 - 5706

33
[ 117322-30-2 ]
[ 177423-00-6 ]
tert-butyl (3R,4S,5S)-4-[{N-[(1-[(9H-fluoren-9-ylmethoxy)carbonyl]amino}cyclopentyl)carbonyl]-L-valyl}(methyl)amino]-3-methoxy-5-methylheptanoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
91%	With N-ethyl-N,N-diisopropylamine; HATU; In dichloromethane; for 18h;	To 6 (287 mg, 0.801 mmol, 1 eq.) in dichloromethane (4 mL, 0.2 M) were added l- [(9H-fluoren-9-ylmethoxy)carbonyl]amino}cyclopentanecarboxylic acid (309 mg, 0.879 mmol, 1.1 eq.), diisopropylethylamine (281 mu, 1.60 mmol, 2 eq.) and HATU (376 mg, 0.960 mmol, 1.2 eq.). The mixture was stirred for 18 hours and diluted with ethyl acetate (15 mL). The reaction mixture was washed with 1 M aqueous hydrochloric acid solution (2 x 5 mL) and with brine (5 mL). The organic layer was dried over sodium sulfate, filtered, and concentrated in vacuo. The crude material was purified by silica gel chromatography (Gradient: 0% to 60% ethyl acetate in heptane) to provide 27 (502 mg, 91%) as a white foam. LC-MS: m/z 692.3 [M+H+], 714.3 [M+Na+], 636.3 [(M - 2-methylprop- l-ene)+H+], retention time = 1.13 minutes; *H NMR (400 MHz, DMSO-i), characteristic signals: delta 7.89 (br d, J=7.4 Hz, 2H), 7.67-7.75 (m, 2H), 7.60 (br s, 1H), 7.38-7.44 (m, 2H), 7.30-7.36 (m, 2H), 7.21 (br d, J=8.8 Hz, 1H), 4.44-4.59 (m, 2H), 4.17-4.27 (m, 3H), 3.68-3.78 (br m, 1H), 3.21 (s, 3H), 2.88 (br s, 3H), 2.09-2.20 (m, 2H), 1.39 (s, 9H).

Reference： [1]Patent: WO2013/72813,2013,A2 .Location in patent: Page/Page column 128

34
[ 35661-60-0 ]
[ 117322-30-2 ]
Nα-(9-fluorenylmethyloxycarbonyl)-Nγ-2,2,4,6,7-pentamethyldihydrobenzofuran-5-sulfonyl-L-arginine [ No CAS ]
L-Arg-L-Leu-L-Leu-L-Arg-L-Leu-L-Leu-L-Arg-L-Leu-Ac5c-NH₂; Ac5c = 1-aminocyclopentane-1-carbonyl [ No CAS ]

Reference： [1]Bioconjugate Chemistry,2014,vol. 25,p. 1761 - 1768

35
[ 35661-60-0 ]
[ 117322-30-2 ]
Nα-(9-fluorenylmethyloxycarbonyl)-Nγ-2,2,4,6,7-pentamethyldihydrobenzofuran-5-sulfonyl-L-arginine [ No CAS ]
L-Arg-L-Leu-L-Leu-L-Arg-L-Leu-Ac5c-L-Arg-L-Leu-Ac5c-NH₂; Ac5c = 1-aminocyclopentane-1-carbonyl [ No CAS ]

Reference： [1]Bioconjugate Chemistry,2014,vol. 25,p. 1761 - 1768

36
[ 35661-60-0 ]
[ 117322-30-2 ]
Nα-(9-fluorenylmethyloxycarbonyl)-Nγ-2,2,4,6,7-pentamethyldihydrobenzofuran-5-sulfonyl-L-arginine [ No CAS ]
L-Arg-L-Leu-Ac5c-L-Arg-L-Leu-Ac5c-L-Arg-L-Leu-Ac5c-NH₂; Ac5c = 1-aminocyclopentane-1-carbonyl [ No CAS ]

Reference： [1]Bioconjugate Chemistry,2014,vol. 25,p. 1761 - 1768

37
[ 35661-60-0 ]
[ 117322-30-2 ]
Nα-(9-fluorenylmethyloxycarbonyl)-Nγ-2,2,4,6,7-pentamethyldihydrobenzofuran-5-sulfonyl-L-arginine [ No CAS ]
L-Arg-L-Leu-Ac5c-L-Arg-L-Leu-Ac5c-L-Arg-Ac5c-Ac5c-NH₂; Ac5c = 1-aminocyclopentane-1-carbonyl [ No CAS ]

Reference： [1]Bioconjugate Chemistry,2014,vol. 25,p. 1761 - 1768

38
[ 35661-60-0 ]
[ 117322-30-2 ]
Nα-(9-fluorenylmethyloxycarbonyl)-Nγ-2,2,4,6,7-pentamethyldihydrobenzofuran-5-sulfonyl-L-arginine [ No CAS ]
L-Arg-L-Leu-Ac5c-L-Arg-Ac5c-Ac5c-L-Arg-Ac5c-Ac5c-NH₂; Ac5c = 1-aminocyclopentane-1-carbonyl [ No CAS ]

Reference： [1]Bioconjugate Chemistry,2014,vol. 25,p. 1761 - 1768

39
[ 35661-60-0 ]
[ 117322-30-2 ]
Nα-(9-fluorenylmethyloxycarbonyl)-Nγ-2,2,4,6,7-pentamethyldihydrobenzofuran-5-sulfonyl-L-arginine [ No CAS ]
L-Arg-Ac5c-Ac5c-L-Arg-Ac5c-Ac5c-L-Arg-Ac5c-Ac5c-NH₂; Ac5c = 1-aminocyclopentane-1-carbonyl [ No CAS ]

Reference： [1]Bioconjugate Chemistry,2014,vol. 25,p. 1761 - 1768

40
(2S)-2-amino-N-[(3R,5S)-3-methoxy-1-[(2S)-2-[(1R,2R)-1-methoxy-2-methyl-2-[[(1S)-2-phenyl-1-(1,3-thiazol-2-yl)ethyl]carbamoyl]ethyl]pyrrolidin-1-yl]-5-methyl-1-oxoheptan-4-yl]-N,3-dimethylbutanamide [ No CAS ]
[ 117322-30-2 ]
N-[(1-[(9H-fluoren-9-ylmethoxy)carbonyl]amino}cyclopentyl)-carbonyl]-N-[(3R,4S,5S)-3-methoxy-1-{(2S)-2-[(1R,2R)-1-methoxy-2-methyl-3-oxo-3-[(1S)-2-phenyl-1-(1,3-thiazol-2-yl)ethyl]amino}propyl]pyrrolidin-1-yl}-5-methyl-1-oxoheptan-4-yl]-N-methyl-L-valinamide [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2014,vol. 57,p. 10527 - 10543

41
[ 29022-11-5 ]
[ 35661-60-0 ]
[ 71989-31-6 ]
[ 112160-37-9 ]
[ 117322-30-2 ]
[ 143824-78-6 ]
[ 98-79-3 ]
Fmoc-Tyr(pg)-OH [ No CAS ]
Fmoc-Ser(pg)-OH [ No CAS ]
Fmoc-His(pg)-OH [ No CAS ]
C₅₉H₈₁N₁₇O₁₃ [ No CAS ]

Reference： [1]MedChemComm,2015,vol. 6,p. 1656 - 1665

42
[ 29022-11-5 ]
[ 71989-31-6 ]
[ 117322-30-2 ]
[ 143824-78-6 ]
[ 98-79-3 ]
Fmoc-Tyr(pg)-OH [ No CAS ]
Fmoc-Ser(pg)-OH [ No CAS ]
Fmoc-His(pg)-OH [ No CAS ]
C₆₄H₇₅N₁₇O₁₃ [ No CAS ]

Reference： [1]MedChemComm,2015,vol. 6,p. 1656 - 1665

43
C₄₀H₆₃N₂O₂PolSi [ No CAS ]
[ 117322-30-2 ]
C₆₁H₈₂N₃O₅PolSi [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		General procedure: To the resin 13 (560 mg) in DMF (2.5 mL) were added a solutionof the appropriate Fmoc-protected amino acid (see Tables 1-3)(0.3 M), PyBOP (0.3 M) and HOBt (0.3 M) in dry DMF (4.2 mL). Thesuspensions were stirred for 3 min and then DIPEA (0.6 M) wasadded. The suspensions were stirred for 3 h under an argon atmosphereat rt. The resins were washed successively with DCM(150 mL), MeOH (120 mL), DCM (75 mL) and dried overnight undervacuum to give resins 14, each bearing an appropriate Fmoc-protectedamino acid. To the resins 14 (161 mg, 0.13 mmol) wereadded a solution of piperidine (20%, v/v) in DCM (2.1 mL) and themixtures were stirred for 1 h at rt. After filtration, the resins werewashed successively with DCM (50 mL), MeOH (45 mL), DCM(25 mL) and dried under vacuum to give resins 15. Portions(65 mg) of resins 15 were placed in reactor wells (12 mL) of anautomated synthesizer reaction block (40-well format) (AdvancedChemTech). To each well was added a solution of appropriate carboxylicacid (see Tables 1-3) (0.3 M), PyBOP (0.3 M) and HOBt 6-Cl(0.3 M) and DIPEA (0.6 M) in dry DMF (2 mL). The suspensionswere vortexed at 300 rpm over a period of 5 h under an argonatmosphere. The wells were then filtered to remove the reactivesolution from the resins 16 and washed successively with THF,DCM, MeOH and DCM.

Reference： [1]Steroids,2016,vol. 107,p. 55 - 64

44
(S)-2-cyclohexyl-2-(3,4,5-trimethoxyphenyl)acetic acid [ No CAS ]
[ 101555-63-9 ]
[ 117322-30-2 ]
(S)-N-(1-carbamoylcyclopentyl)-1-((S)-2-cyclohexyl-2-(3,4,5-trimethoxyphenyl)acetyl)piperidine-2-carboxamide [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2016,vol. 59,p. 2410 - 2422

45
[ 29022-11-5 ]
(S)-2-cyclohexyl-2-(3,4,5-trimethoxyphenyl)acetic acid [ No CAS ]
[ 101555-63-9 ]
[ 117322-30-2 ]
(S)-N-(1-((2-amino-2-oxoethyl)carbamoyl)cyclopentyl)-1-((S)-2-cyclohexyl-2-(3,4,5-trimethoxyphenyl)acetyl)piperidine-2-carboxamide [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2016,vol. 59,p. 2410 - 2422

46
Fmoc-N-methyl norleucine [ No CAS ]
[ 29022-11-5 ]
[ 35661-60-0 ]
[ 71989-31-6 ]
[ 35661-40-6 ]
[ 71989-33-8 ]
[ 103213-32-7 ]
[ 84000-07-7 ]
[ 132388-59-1 ]
[ 109425-51-6 ]
[ 117322-30-2 ]
[ 143824-78-6 ]
Nα-(9-fluorenylmethyloxycarbonyl)-Nγ-2,2,4,6,7-pentamethyldihydrobenzofuran-5-sulfonyl-L-arginine [ No CAS ]
C₉₂H₁₃₀N₂₄O₁₈S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
6.4 mg		General procedure: Example 1001 was prepared on Rink Resin following the general synthetic procedures: Fmoc-Gly-OH "Symphony Method B: Resin-swelling procedure" was followed Fmoc-Cys(Trt)-OH "Symphony Method B: Standard-coupling procedure " was followed Fmoc-Arg(Pbf)-OH "Symphony Method B: Standard-coupling procedure " was followed Fmoc-nMethyl-Nle-OH "Symphony Method B: Standard-coupling procedure " was followed Fmoc-nMethyl-Nle-OH "Symphony Method B: Secondary amine-coupling procedure", was followed Fmoc-Trp(Boc)-OH "Symphony Method B: Secondary amine-coupling procedure", was followed Fmoc-Ser(tBu)-OH "Symphony Method B: Standard-coupling procedure " was followed Fmoc-Trp(Boc)-OH "Symphony Method B: Standard-coupling procedure " was followed Fmoc-Cyclopenty-Gly-OH "Manual Coupling procedure A" was followed Fmoc-Leu-OH "Symphony Method B: Secondary amine-coupling procedure", was followed Fmoc-His(Trt)-OH "Symphony Method B: Standard-coupling procedure " was followed Fmoc-Pro-OH "Symphony Method B: Standard-coupling procedure " was followed Fmoc-Asn(Trt)-OH "Symphony Method B: Secondary amine-coupling procedure", was followed Fmoc-nMethyl-Ala-OH "Symphony Method B: Standard-coupling procedure " was followed Fmoc-Phe-OH "Symphony Method B: Secondary amine-coupling procedure" was followed "Symphony Method B: Final capping procedure" was followed "Global Deprotection Method F" was followed "Cyclization Method D" was followed The crude material was purified via preparative LC/MS with the following conditions: Column: Waters XBridge C18, 19 x 250 mm, 5-mupiiota particles; Mobile Phase A: 5:95 acetonitrile: water with 0.1% trifluoroacetic acid; Mobile Phase B: 95:5 acetonitrile: water with 0.1% trifluoroacetic acid; Gradient: 15- 65% B over 25 minutes, then a 5-minute hold at 100% B; Flow: 20 mL/min. Fractions containing the desired product were combined and dried via centrifugal evaporation. The yield of the product was 6.4 mg, and its estimated purity by LCMS analysis was 100%. Analysis LCMS Condition D : Retention time = 1.67 mm; ESI-MS(+) m/z 947.2 (M+2H). Analysis LCMS Condition E. : Retention time = 1.57 min; ESI-MS(+) m/z 946.7 (M+2H).

Reference： [1]Patent: WO2016/100608,2016,A1 .Location in patent: Page/Page column 99-100

47
[ 35661-60-0 ]
[ 35661-39-3 ]
[ 71195-85-2 ]
[ 35661-40-6 ]
[ 117322-30-2 ]
acryloyl-Phe-Leu-Ala-Phe-Acpc [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2017,vol. 56,p. 728 - 732
Angew. Chem.,2017,vol. 129,p. 746 - 750,5

48
[ 117322-30-2 ]
C₃₂H₄₆N₄O₆S [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2018,vol. 140,p. 3690 - 3711

49
[ 117322-30-2 ]
methyl (2S,4R)-4-[({2-[(1R,3R)-1-acetoxy-3-[(1-[(9H-fluoren-9-ylmethoxy)carbonyl]amino}cyclopentyl)carbonyl](methyl)amino}-4-methylpentyl]-1,3-thiazol-4-yl}carbonyl)amino]-2-methyl-5-phenylpentanoate [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2018,vol. 140,p. 3690 - 3711

50
[ 117322-30-2 ]
methyl (2S,4R)-4-[({2-[(1R,3R)-1-acetoxy-4-methyl-3-(methyl[1-([(2R)-1-methylpiperidin-2-yl]-carbonyl}amino)cyclopentyl]carbonyl}amino)pentyl]-1,3-thiazol-4-yl}carbonyl)amino]-2-methyl-5-phenylpentanoate [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2018,vol. 140,p. 3690 - 3711

51
[ 86123-10-6 ]
[ 109425-51-6 ]
[ 117322-30-2 ]
[ 146982-24-3 ]
[ 143824-78-6 ]
Nα-(9-fluorenylmethyloxycarbonyl)-Nγ-2,2,4,6,7-pentamethyldihydrobenzofuran-5-sulfonyl-L-arginine [ No CAS ]
[Ac₅c-His-DPhe-Arg-Trp-Asp]-amide [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2018,vol. 61,p. 4263 - 4269

52
[ 109425-51-6 ]
[ 117322-30-2 ]
[ 146982-24-3 ]
[ 143824-78-6 ]
N-[(9-fluorenyl)methoxycarbonyl]-3-(2-naphthyl)-D-alanine [ No CAS ]
Nα-(9-fluorenylmethyloxycarbonyl)-Nγ-2,2,4,6,7-pentamethyldihydrobenzofuran-5-sulfonyl-L-arginine [ No CAS ]
[Ac5c-His-DNal(2’)-Arg-Trp-Asp]-amide [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2018,vol. 61,p. 4263 - 4269

53
[ 86123-10-6 ]
[ 109425-51-6 ]
[ 117322-30-2 ]
[ 133464-46-7 ]
[ 143824-78-6 ]
Nα-(9-fluorenylmethyloxycarbonyl)-Nγ-2,2,4,6,7-pentamethyldihydrobenzofuran-5-sulfonyl-L-arginine [ No CAS ]
[Ac₅c-His-D-Phe-Arg-Trp-Glu]-amide [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2018,vol. 61,p. 4263 - 4269

54
[ 109425-51-6 ]
[ 117322-30-2 ]
[ 133464-46-7 ]
[ 143824-78-6 ]
N-[(9-fluorenyl)methoxycarbonyl]-3-(2-naphthyl)-D-alanine [ No CAS ]
Nα-(9-fluorenylmethyloxycarbonyl)-Nγ-2,2,4,6,7-pentamethyldihydrobenzofuran-5-sulfonyl-L-arginine [ No CAS ]
[Ac5c-His-D-Nal(2’)-Arg-Trp-Glu]-amide [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2018,vol. 61,p. 4263 - 4269

55
[ 35661-60-0 ]
[ 35661-39-3 ]
[ 64-19-7 ]
[ 117322-30-2 ]
Nα-(9-fluorenylmethyloxycarbonyl)-Nγ-2,2,4,6,7-pentamethyldihydrobenzofuran-5-sulfonyl-L-arginine [ No CAS ]
[ 378247-75-7 ]
Ac-Ala-Arg-Leu-P₁-(7-amino-4-carbamoylmethylcoumarin), P₁ = Ac₅C [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2018,vol. 61,p. 5222 - 5234

56
[ 29022-11-5 ]
[ 35661-40-6 ]
[ 71989-38-3 ]
[ 117322-30-2 ]
C₂₈H₃₅N₅O₇ [ No CAS ]

Reference： [1]Peptide Science,2019,vol. 111

57
[ 117322-30-2 ]
(cyanomethyl)dimethylsulfonium bromide [ No CAS ]
C₂₅H₂₆N₂O₃S [ No CAS ]

Reference： [1]Chemistry - A European Journal,2019,vol. 25,p. 15504 - 15507

58
[ 117322-30-2 ]
C₂₂H₂₁NO₅ [ No CAS ]

Reference： [1]Chemistry - A European Journal,2019,vol. 25,p. 15504 - 15507

59
[ 117322-30-2 ]
C₃₁H₃₂N₂O₅ [ No CAS ]

Reference： [1]Chemistry - A European Journal,2019,vol. 25,p. 15504 - 15507

Same Skeleton Products

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Historical Records

Related Functional Groups of
[ 117322-30-2 ]

Amino Acid

[ 35661-60-0 ]

Fmoc-Leu-OH

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[ 114360-54-2 ]

Fmoc-D-Leu-OH

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[ 108321-39-7 ]

Fmoc-D-Asparagine

Similarity: 0.90

[ 35661-39-3 ]

Fmoc-Ala-OH

Similarity: 0.88

[ 79990-15-1 ]

Fmoc-D-Ala-OH

Similarity: 0.88

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P340	Remove victim to fresh air and keep at rest in a position comfortable for breathing.
P341	If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P342	If experiencing respiratory symptoms:
P350	Gently wash with plenty of soap and water.
P351	Rinse cautiously with water for several minutes.
P352	Wash with plenty of soap and water.
P353	Rinse skin with water/shower.
P360	Rinse immediately contaminated clothing and skin with plenty of water before removing clothes.
P361	Remove/Take off immediately all contaminated clothing.
P362	Take off contaminated clothing and wash before reuse.
P363	Wash contaminated clothing before reuse.
P370	In case of fire:
P371	In case of major fire and large quantities:
P372	Explosion risk in case of fire.
P373	DO NOT fight fire when fire reaches explosives.
P374	Fight fire with normal precautions from a reasonable distance.
P376	Stop leak if safe to do so. Oxidising gases (section 2.4) 1
P377	Leaking gas fire: Do not extinguish, unless leak can be stopped safely.
P378
P380	Evacuate area.
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P390	Absorb spillage to prevent material damage.
P391	Collect spillage. Hazardous to the aquatic environment
P301 + P310	IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.
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P301 + P330 + P331	IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.
P302 + P334	IF ON SKIN: Immerse in cool water/wrap in wet bandages.
P302 + P350	IF ON SKIN: Gently wash with plenty of soap and water.
P303 + P361 + P353	IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P304 + P312	IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell.
P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P304 + P341	IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P306 + P360	IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes.
P307 + P311	IF exposed: call a POISON CENTER or doctor/physician.
P308 + P313	IF exposed or concerned: Get medical advice/attention.
P309 + P311	IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician.
P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
P337 + P313	IF eye irritation persists: Get medical advice/attention.
P342 + P311	IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.
P370 + P376	In case of fire: Stop leak if safe to Do so.
P370 + P378	In case of fire:
P370 + P380	In case of fire: Evacuate area.
P370 + P380 + P375	In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion.
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P401
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Purity	Size	Price	VIP Price	USA Stock *0-1 Day	Global Stock *5-7 Days	Quantity
{[ item.p_purity ]}	{[ item.pr_size ]}	{[ getRatePrice(item.pr_usd, 1,1) ]} {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate) ]}	{[ getRatePrice(item.pr_usd, 1,1) ]}	Inquiry {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate) ]} {[ getRatePrice(item.pr_usd,1,item.mem_rate) ]}	{[ item.pr_usastock ]}	Inquiry -	{[ item.pr_chinastock ]}	Inquiry -

Physical hazards
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H200	Unstable explosive
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H316	Causes mild skin irritation
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Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

[ CAS No. 117322-30-2 ] {[proInfo.proName]}

Quality Control of [ 117322-30-2 ]

Related Doc. of [ 117322-30-2 ]

Product Details of [ 117322-30-2 ]

Safety of [ 117322-30-2 ]

Application In Synthesis of [ 117322-30-2 ]

[ 117322-30-2 ] Synthesis Path-Upstream 1~3

[ 117322-30-2 ] Synthesis Path-Downstream 1~59

Related Functional Groups of [ 117322-30-2 ]

Amino Acid

Precautionary Statements-General

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Response

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Inquiry

Related Functional Groups of
[ 117322-30-2 ]