[ CAS No. 917222-23-2 ] {[proInfo.proName]}

Name: 917222-23-2|2,5-Dioxopyrrolidin-1-yl hept-6-ynoate|95+%
Brand: Ambeed
SKU: A1161129
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Quality Control of [ 917222-23-2 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 917222-23-2 ]

SDS Specification

Alternatived Products of [ 917222-23-2 ]

Product Details of [ 917222-23-2 ]

CAS No. :	917222-23-2	MDL No. :	MFCD29041721
Formula :	C₁₁H₁₃NO₄	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	KENPLOYECFEPSG-UHFFFAOYSA-N
M.W :	223.23	Pubchem ID :	86636878
Synonyms :

Safety of [ 917222-23-2 ]

Signal Word:	Warning	Class:
Precautionary Statements:	P261-P264-P270-P271-P280-P301+P312-P302+P352-P304+P340-P330-P363-P501	UN#:
Hazard Statements:	H302-H312-H332	Packing Group:
GHS Pictogram:

Application In Synthesis of [ 917222-23-2 ]

* 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.

Downstream synthetic route of [ 917222-23-2 ]

[ 917222-23-2 ] Synthesis Path-Downstream 1~14

1
[ 6066-82-6 ]
[ 30964-00-2 ]
[ 917222-23-2 ]

Yield	Reaction Conditions	Operation in experiment
72%	With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; at 20℃; for 18h;	<strong>[30964-00-2]6-heptynoic acid</strong> (5) (> 97%, TCI, Portland, OR) (1 g, 7.9 mmol, 1 equiv.) was dissolved in 100 ml of anhydrous methylene chloride. N-hydroxysuccinimide (NHS) (98+%, Acros, New Jersey) (2.3 g, 19.8 mmol, 2.5 equiv.) and l-(3-dimethylaminopropyl)- 3-ethylcarbodiimide hydrochloride (EDC) (98+%, Alfa Aesar) (2.3 g, 11.9 mmol, 1.5 equiv.) was added to the above solution. The resulting reaction mixture was stirred at room temperature overnight (18 hours) before 500 ml of a saturated sodium bicarbonate aqueous solution was added to it. The aqueous phase was extracted with 500 ml of ether. The ether extract was combined with the methylene chloride phase, washed with 500 ml of water and 500 ml of brine, and then dried with anhydrous magnesium sulfate. After magnesium <n="35"/>sulfate was filtered away and the solvent was removed by rotary evaporation, an off-white solid (1.3 g, 72 % yield) was obtained after being further dried overnight under vacuum. This solid was then used directly in the next step.

Reference： [1]Bioconjugate Chemistry,2016,vol. 27,p. 1624 - 1637
[2]Journal of the American Chemical Society,2006,vol. 128,p. 14468 - 14469
[3]Patent: WO2007/56389,2007,A2 .Location in patent: Page/Page column 32-33

2
[ 917222-23-2 ]
[ 77835-31-5 ]
[ 934220-54-9 ]

Yield	Reaction Conditions	Operation in experiment
57%	With triethylamine In methanol at 20℃; for 3h;

Reference： [1]Luo, Yuan; Knuckley, Bryan; Bhatia, Monica; Pellechia, Perry J.; Thompson, Paul R. [Journal of the American Chemical Society, 2006, vol. 128, # 45, p. 14468 - 14469]

3
[ 917222-23-2 ]
N-(5-aminopentyl)hept-6-ynamide hydrochloride [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 57 percent / triethylamine / methanol / 3 h / 20 °C 2: 75 percent / HCl / dioxane / 5 h / 20 °C

Reference： [1]Luo, Yuan; Knuckley, Bryan; Bhatia, Monica; Pellechia, Perry J.; Thompson, Paul R. [Journal of the American Chemical Society, 2006, vol. 128, # 45, p. 14468 - 14469]

4
[ 917222-23-2 ]
[ 934220-54-9 ]

Yield	Reaction Conditions	Operation in experiment
57%	Stage #1: N-(tert-butoxycarbonyl)-1,5-diaminopentane hydrochloride With triethylamine In methanol at 20℃; for 0.25h; Stage #2: 1-(hept-6-ynoyloxy)pyrrolidine-2,5-dione In methanol for 3h;	iV-l-Boc-l,5-diaminopentane hydrogen chloride (7) (> 99%, BACHEM, Torrance,CA) (215 mg, 0.9 mmol, 2 equiv.) was dissolved in 20 ml of anhydrous methanol. To this solution 0.2 ml of dry triethylamine (1.35 mmol, 3 equiv.) was added and the reaction mixture was stirred at room temperature for 15 minutes before 6-heptynoic acid succinimidyl ester (6) (100 mg, 0.45 mmol, 1 equiv.) was added. After the reaction proceeded for 3 hours, the solvent was removed by rotary evaporation and the resulting crude product was dried under vacuum for 2 hours. Purification by column chromatography (neutral alumina, CHCl3ZMeOH (98%/2%)) afforded a Boc-protected form of 8 - 6-heptynoic acid (5-(Boc)amino-pentyl)-amide (80 mg, 57 % yield). (MS- ES+: m/z 311 (M+l)).

Reference： [1]Current Patent Assignee: UNIVERSITY OF SOUTH CAROLINA - WO2007/56389, 2007, A2 Location in patent: Page/Page column 33

5
[ 917222-23-2 ]
cRGD [ No CAS ]
C₃₄H₄₉N₉O₈ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine In N,N-dimethyl-formamide at 20℃;

Reference： [1]Current Patent Assignee: GOVERNMENT OF THE UNITED STATES - WO2011/68978, 2011, A1 Location in patent: Page/Page column 8

6
[ 917222-23-2 ]
[ 1254943-35-5 ]
[ 1379771-85-3 ]

Yield	Reaction Conditions	Operation in experiment
8 mg	With N-ethyl-N,N-diisopropylamine In 1,2-dichloro-ethane at 20℃; Inert atmosphere;

Reference： [1]Willems, Lianne I.; Li, Nan; Florea, Bogdan I.; Ruben, Mark; Van Der Marel, Gijsbert A.; Overkleeft, Herman S. [Angewandte Chemie - International Edition, 2012, vol. 51, # 18, p. 4431 - 4434]

7
[ 917222-23-2 ]
N-[(1S,2R,3R,4R,5S)-1-(13-{4-[(3-[(1-{1-[(1S,2R,3R,4R,5S)-4-(acetylamino)-2,3-dihydroxy-6,8-diox-abicyclo[3.2.1]oct-1-yl]-2,5,8,11-tetraoxatridecan13-yl}-1H-1,2,3-triazol-4-yl)methoxy]-2-[(1-{1-[(1S,2R,3R,4R,5S)-4-(acetylamino)-2,3-dihydroxy-6,8-dioxabicyclo[3.2.1]oct-1-yl]-2,5,8,11-tetraoxatridecan-13-yl}-1H-1,2,3-triazol-4-yl)methoxy]methyl}-2-aminopropoxy)methyl]-1H-1,2,3-triazol-1-yl}-2,5,8,11-tetraoxatridec-1-yl)-2,3-dihydroxy-6,8-dioxabicyclo[3.2.1]oct-4-yl]acetamide hydrochloricacidsalt [ No CAS ]
N-(1,3-bis[(1-{1-[(1S,2R,3R,4R,5S)-4-(acetylamino)-2,3-dihydroxy-6,8-dioxabicyclo[3.2.1]oct-1-yl]-2,5,8,11-tetraoxatridecan-13-yl}-1H-1,2,3-triazol-4-yl)methoxy]-2-[(1-{1-[(1 S,2R,3R,4R,5S)-4-(acetylamino)-2,3-dihydroxy-6,8-dioxabicyclo[3.2.1]oct-1-yl]-2,5,8,11-tetraoxatridecan-13-yl}-1H-1,2,3-triazol-4-yl)methoxy]methyl}propan-2-yl)hept-6-ynamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
19%	Stage #1: N-[(1S,2R,3R,4R,5S)-1-(13-{4-[(3-[(1-{1-[(1S,2R,3R,4R,5S)-4-(acetylamino)-2,3-dihydroxy-6,8-diox-abicyclo[3.2.1]oct-1-yl]-2,5,8,11-tetraoxatridecan13-yl}-1H-1,2,3-triazol-4-yl)methoxy]-2-[(1-{1-[(1S,2R,3R,4R,5S)-4-(acetylamino)-2,3-dihydroxy-6,8-dioxabicyclo[3.2.1]oct-1-yl]-2,5,8,11-tetraoxatridecan-13-yl}-1H-1,2,3-triazol-4-yl)methoxy]methyl}-2-aminopropoxy)methyl]-1H-1,2,3-triazol-1-yl}-2,5,8,11-tetraoxatridec-1-yl)-2,3-dihydroxy-6,8-dioxabicyclo[3.2.1]oct-4-yl]acetamide hydrochloricacidsalt With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide for 0.166667h; Stage #2: 1-(hept-6-ynoyloxy)pyrrolidine-2,5-dione In N,N-dimethyl-formamide at 23 - 60℃; for 50h;	N-(1,3-bis[(1-{1-[(1S,2R,3R,4R,5S)-4-(acetylamino)-2,3-dihydroxy-6,8-dioxabicyclo[3.2.1]oct-1-yl]-2,5,8,11-tetraoxatridecan-13-yl}-1H-1,2,3-triazol-4-yl)methoxy]-2-[(1-{1-[(1 S,2R,3R,4R,5S)-4-(acetylamino)-2,3-dihydroxy-6,8-dioxabicyclo[3.2.1]oct-1-yl]-2,5,8,11-tetraoxatridecan-13-yl}-1H-1,2,3-triazol-4-yl)methoxy]methyl}propan-2-yl)hept-6-ynamide (45) N-(1,3-bis[(1-{1-[(1S,2R,3R,4R,5S)-4-(acetylamino)-2,3-dihydroxy-6,8-dioxabicyclo[3.2.1]oct-1-yl]-2,5,8,11-tetraoxatridecan-13-yl}-1H-1,2,3-triazol-4-yl)methoxy]-2-[(1-{1-[(1 S,2R,3R,4R,5S)-4-(acetylamino)-2,3-dihydroxy-6,8-dioxabicyclo[3.2.1]oct-1-yl]-2,5,8,11-tetraoxatridecan-13-yl}-1H-1,2,3-triazol-4-yl)methoxy]methyl}propan-2-yl)hept-6-ynamide (45) To a solution of N-[(1S,2R,3R,4R,5S)-1-(13-{4-[(3-[(1-{1-[(1S,2R,3R,4R,5S)-4-(acetylamino)-2,3-dihydroxy-6,8-dioxabicyclo[3.2.1]oct-1-yl]-2,5,8,11-tetraoxatridecan-13-yl}-1H-1,2,3-triazol-4-yl)methoxy]-2-[(1-{1-[(1S,2R,3R,4R,5S)-4-(acetylamino)-2,3-dihydroxy-6,8-dioxabicyclo[3.2.1]oct-1-yl]-2,5,8,11-tetraoxatridecan-13-yl}-1H-1,2,3-triazol-4-yl)methoxy]methyl}-2-aminopropoxy)methyl]-1H-1,2,3-triazol-1-yl}-2,5,8,11-tetraoxatridec-1-yl)-2,3-dihydroxy-6,8-dioxabicyclo[3.2.1]oct-4-yl]acetamide hydrochloric acid salt (42) (25 mg, 0.016 mmol) in N,N-dimethylformamide (0.5 mL) was added N,N-diisopropylethylamine (0.0111 mL, 0.0635 mmol) and was allowed to stir for 10 minutes before being added to neat 1-(hept-6-ynoyloxy)pyrrolidine-2,5-dione (see PCT Int. Appl., 2007056389, 18 May 2007, 5.31 mg, 0.0238 mmol) and the reaction was allowed to stir at room temperature for 18 hours. The reaction was then heated to 60° C. for 32 hours. After 32 hours, the reaction was concentrated under reduced pressure. The crude material was diluted with dimethylsulfoxide (1 mL) and passed through a syringe filter and the crude material was purified using reverse-phase chromatography using the conditions seen below yielding the title compound as a gum (5 mg, 19%).Purification Conditions:10317] The residue was dissolved in dimethyl sulfoxide (1 mE) and purified by reversed-phase HPEC (Column: Waters Sunfire C18 19x100, 5 u; Mobile phase A: 0.05% TFA in water (v/v); Mobile phase B: 0.05% TFA in acetonitrile (v/v); 95.0% H20/5 .0%Acetonitrile linear to 55% H20/45%Aceto- nitrile in 10.5 mm, 55% H20/45% Acetonitrile linear to 0% H20/i00% MeCN in 0.5 mm, Hold at 0% H20/i00%Aceto- nitrile from 11.0 mm to 12.0 mm. Flow: 25 mE/mm.QC Conditions:10318] Column: Waters Atlantis dCi8 4.6x50, 5 u; Mobile phase A: 0.05% TFA in water (v/v); Mobile phase B: 0.05% TFA in acetonitrile (v/v); 95.0% H20/5.0% Acetonitrile linear to 5% H20/95% Acetonitrile in 4.0 mm, Hold at 5% H20/95% Acetonitrile from 4.0 mm to 5.0 mm. Flow: 2 mE/mm.; Retention time=i.68; Mass observed=824.2237. Method C: 3 minute run ERMS [M=823]. ‘H NMR (METHANOE-d4) ö: 7.99 (s, 3H), 5.21 (s, 3H), 4.59 (t, J=5.0 Hz, 6H), 4.56 (s, 6H), 3.95 (t, J=i0.0 Hz, 6H), 3.85-3.92 (m, 9H), 3.74-3.79 (m, 9H), 3.71 (dd, J=i0.0, 4.1 Hz, 3H), 3.54-3.67 (m, 41H), 2.13-2.24 (m, 6H), 1.99 (s, 9H), 1.66 (quin, J=7.5 Hz, 2H), 1.50 (quin, J=7.3 Hz, 2H)

Reference： [1]Current Patent Assignee: PFIZER INC - US2015/329555, 2015, A1 Location in patent: Paragraph 0315; 0316; 0317; 0318

8
[ 917222-23-2 ]
[ 123-78-4 ]
C₂₅H₄₅NO₃ [ No CAS ]