[ CAS No. 430430-57-2 ] {[proInfo.proName]}

Name: 430430-57-2|2,2-Dimethyl-4-oxo-3,8,11-trioxa-5-azatridecan-13-yl methanesulfonate|95%
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SKU: A1523589
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2D 3D

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Quality Control of [ 430430-57-2 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 430430-57-2 ]

Product Details of [ 430430-57-2 ]

CAS No. :	430430-57-2	MDL No. :	N/A
Formula :	C₁₂H₂₅NO₇S	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	KZDCXZWVOMGZBF-UHFFFAOYSA-N
M.W :	327.39	Pubchem ID :	56647370
Synonyms :

Calculated chemistry of [ 430430-57-2 ]

Physicochemical Properties

Num. heavy atoms :	21
Num. arom. heavy atoms :	0
Fraction Csp3 :	0.92
Num. rotatable bonds :	13
Num. H-bond acceptors :	7.0
Num. H-bond donors :	1.0
Molar Refractivity :	76.53
TPSA :	108.54 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	No
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-8.25 cm/s

Lipophilicity

Log Po/w (iLOGP) :	3.39
Log Po/w (XLOGP3) :	0.06
Log Po/w (WLOGP) :	1.6
Log Po/w (MLOGP) :	0.02
Log Po/w (SILICOS-IT) :	0.44
Consensus Log Po/w :	1.1

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	1.0
Egan :	0.0
Muegge :	0.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-1.05
Solubility :	29.2 mg/ml ; 0.0892 mol/l
Class :	Very soluble
Log S (Ali) :	-1.89
Solubility :	4.19 mg/ml ; 0.0128 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-2.77
Solubility :	0.557 mg/ml ; 0.0017 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	3.59

Safety of [ 430430-57-2 ]

Signal Word:	Warning	Class:
Precautionary Statements:	P261-P264-P270-P271-P280-P301+P312-P302+P352-P304+P340-P305+P351+P338-P330-P332+P313-P337+P313-P362-P403+P233-P405-P501	UN#:
Hazard Statements:	H302-H315-H319-H335	Packing Group:
GHS Pictogram:

Application In Synthesis of [ 430430-57-2 ]

* 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 [ 430430-57-2 ]
Downstream synthetic route of [ 430430-57-2 ]

[ 430430-57-2 ] Synthesis Path-Upstream 1~1

1
[ 430430-57-2 ]
[ 189209-27-6 ]

Reference： [1] Bioorganic and Medicinal Chemistry Letters, 2012, vol. 22, # 1, p. 586 - 590

[ 430430-57-2 ] Synthesis Path-Downstream 1~8

1
[ 124-63-0 ]
[ 139115-92-7 ]
[ 430430-57-2 ]

Yield	Reaction Conditions	Operation in experiment
99%	With triethylamine; In dichloromethane; at 0 - 20℃; for 1h;	To a solution of <strong>[139115-92-7]tert-butyl N-[2-[2-(2-hydroxyethoxy)ethoxy]ethyl]carbamate</strong> (4.00 g, 16.0 mmol, CAS139115-92-7) in dichloromethane (5 mL) was added triethylamine (3.25 g, 32.0 mmol) and MsCl (2.21 g, 19.2 mmol) at 0 C. The reaction mixture was then allowed to warm to rt and stirred for 1. On completion, the reaction mixture was quenched with water (10 mL) and extracted with dichloromethane (3×100 mL). The combined organic layer was washed with brine (2×50 mL), dried over anhydrous sodium sulfate, filtered and concentrated in vacuo to give the title compound (5.23 g, 99% yield) as a colorless oil. 1H NMR (400 MHz, CDCl3) delta 4.94 (s, 1H), 4.44-4.37 (m, 2H), 3.83-3.75 (m, 2H), 3.69-3.65 (m, 2H), 3.64-3.59 (m, 2H), 3.54 (t, J=5.2 Hz, 2H), 3.36-3.29 (m, 2H), 3.08 (s, 3H), 1.45 (s, 9H).
98%	With triethylamine; In dichloromethane; at 0 - 20℃; for 2h;	To a mixture of <strong>[139115-92-7]tert-butyl N-[2-[2-(2-hydroxyethoxy)ethoxy]ethyl]carbamate</strong> (2.00 g, 8.02 mmol, CAS139115-92-7) and triethylamine (2.44 g, 24.0 mmol) in DCM (20 mL) was added mesyl chloride (1.10 g, 9.63 mmol) at 0 C. The reaction mixture was then allowed to warm to rt and stirred for 2 h. On completion, the reaction mixture was poured into water (15 mL) and extracted with DCM (3×20 mL). The combined organic layer was dried over Na2SO4, filtered and concentrated in vacuo to give the title compound (2.60 g, 98% yield) as a light yellow oil. 1H NMR (400 MHz, CDCl3) delta 4.87 (s, 1H), 4.35-4.29 (m, 2H), 3.73-3.66 (s, 2H), 3.63-3.52 (m, 4H), 3.50-3.43 (m, 2H), 3.30-3.20 (s, 2H), 3.01 (s, 3H), 1.38 (s, 9H).
93%	With triethylamine; In dichloromethane; at 20℃; for 2h;	To a stirred solution of tert-butyl(2-(2-(2-hydroxyethoxy)ethoxy)ethyl)carbamate (1.8 g, 7.2 mmol) and triethylamine (3.0 g, 4.15 mL, 21.7 mmol) in DCM (12 mL) was added of mesyl chloride (0.85 g, 10.8 mmol) and the reaction mixture was stirred at rt for 2 h. The reaction mixture was then transferred into ice water and the resulting mixture was extracted using DCM (3×25 mL). The combined organic layer was dried over anhydrous sodium sulfate and filtered. The filtrate was evaporated under reduced pressure to give 2,2-dimethyl-4-oxo-3,8,11-trioxa-5-azatridecan-13-yl methanesulfonate as a yellow semisolid (2.2 g, 93%).

78%

With triethylamine; In dichloromethane; at 0 - 20℃;Inert atmosphere;

Methanesulfonyl chloride (0.18 mL, 2.29 mmol) was added slowly dropwise to a stirred solution of 8-tert-butoxycarbonylamino-3,6-dioxaoctan-1-ol (0.52 g, 2.08 mmol) and TEA (0.44 mL, 3.12 mmol) in anhydrous CH2Cl2 (10 mL) at 0 C under N2 atmosphere. The reaction mixture was allowed to slowly warm to rt before being left to stir overnight. After this time, the reaction was quenched by the addition of ice cool water (10 mL) and the two phases were separated. The organic layer was washed with a saturated aqueous solution of NaHCO3 (10 mL) followed by brine (10 mL) and dried (MgSO4). The solvent was removed under reduced pressure and the crude residue obtained was purified by column chromatography (EtOAc/petroleum ether (40-60 C), 4:6) to give the intermediate, 8-tert-butoxycarbonylamino-3,6-dioxaoct-1-yl methanesulfonate (0.53 g, 78%), as a colourless oil: Rf 0.46 (EtOAc/MeOH, 95:5); numax (film) 2976, 2935, 2874, 1708, 1521, 1352, 1175 cm-1; deltaH (200 MHz; CDCl3) 1.38 (9H, s, C(CH3)3), 3.01 (3H, s, OSO2CH3), 3.24 (2H, br dt, NHCH2CH2O), 3.47 (2H, t, J 5.3, NHCH2CH2O), 3.58-3.61 (4H, m, OCH2CH2O), 3.71 (2H, t, J 4.6, OCH2CH2OSO2), 4.33 (2H, t, J 4.6, OCH2CH2OSO2), 4.93 (1H, br s, NH); deltaC (50 MHz; CDCl3) 28.6, 37.9, 40.5, 69.2, 69.4, 70.4, 70.5, 70.8, 79.5, 155.8; m/z (CI) 345 ([M+NH3]+, 17%), 328 ([M+H]+, 20), 289 (70), 271 (100), 228 (35); HRMS (ESI) m/z: [M+H]+, found 328.1426. C12H26NO7S requires 328.1424.

Reference： [1]Patent: US2019/192668,2019,A1 .Location in patent: Paragraph 2093; 2094
[2]Patent: US2019/192668,2019,A1 .Location in patent: Paragraph 2112; 2113
[3]Bioorganic and Medicinal Chemistry Letters,2008,vol. 18,p. 1084 - 1090
[4]Patent: US2019/192668,2019,A1 .Location in patent: Paragraph 2069; 2071
[5]Journal of Medicinal Chemistry,2009,vol. 52,p. 7029 - 7043
[6]MedChemComm,2019,vol. 10,p. 1037 - 1041
[7]Tetrahedron,2011,vol. 67,p. 9588 - 9594
[8]Bioorganic and Medicinal Chemistry Letters,2006,vol. 16,p. 1324 - 1328
[9]Bioorganic and Medicinal Chemistry Letters,2009,vol. 19,p. 92 - 95
[10]European Journal of Organic Chemistry,2011,p. 1641 - 1644
[11]Bioorganic and Medicinal Chemistry Letters,2012,vol. 22,p. 586 - 590
[12]European Journal of Organic Chemistry,2013,p. 7952 - 7959

2
[ 430430-57-2 ]
[ 112-27-6 ]
[ 331242-61-6 ]

Yield	Reaction Conditions	Operation in experiment
67%	With sodium hydroxide In water; toluene at 100℃;
	Stage #1: 2,2'-[1,2-ethanediylbis(oxy)]bisethanol With sodium hydroxide In water at 100℃; for 1h; Stage #2: 2,2-dimethyl-4-oxo-3,8,11-trioxa-5-azatridecane-13-yl methanesulfonate In water; toluene at 100℃; for 18.5h;
	With sodium hydroxide In toluene at 100℃;

Reference： [1]Gérard, Estelle; Meulle, Aline; Feron, Olivier; Marchand-Brynaert, Jacqueline [Bioorganic and Medicinal Chemistry Letters, 2012, vol. 22, # 1, p. 586 - 590]
[2]Rerat, Vincent; Dive, Georges; Cordi, Alex A.; Tucker, Gordon C.; Bareille, Reine; Amédée, Joëlle; Bordenave, Laurence; Marchand-Brynaert, Jacqueline [Journal of Medicinal Chemistry, 2009, vol. 52, # 22, p. 7029 - 7043]
[3]Hammaecher, Catherine; Joris, Bernard; Goormaghtigh, Erik; Marchand-Brynaert, Jacqueline [European Journal of Organic Chemistry, 2013, # 35, p. 7952 - 7959]

3
[ 430430-57-2 ]
[ 1091627-77-8 ]

Reference： [1]European Journal of Organic Chemistry,2011,p. 1641 - 1644

4
[ 430430-57-2 ]
[ 112-60-7 ]
[ 1292268-13-3 ]

Yield	Reaction Conditions	Operation in experiment
86%	Stage #1: Tetraethylene glycol With sodium hydroxide In water; toluene at 100℃; for 1h; Stage #2: 2,2-dimethyl-4-oxo-3,8,11-trioxa-5-azatridecane-13-yl methanesulfonate In water; toluene at 20 - 100℃;

Reference： [1]Moreau, Julie; Marchand-Brynaert, Jacqueline [European Journal of Organic Chemistry, 2011, # 9, p. 1641 - 1644]

5
[ 430430-57-2 ]
[ 189209-27-6 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2012,vol. 22,p. 586 - 590

6
[ 430430-57-2 ]
[ 932741-19-0 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: sodium hydride / tetrahydrofuran; mineral oil / 0.5 h / 0 °C / Inert atmosphere 1.2: 20 °C / Inert atmosphere 2.1: trifluoroacetic acid / dichloromethane / 2 h / 20 °C

Reference： [1]Steinebach, Christian; Sosič, Izidor; Lindner, Stefanie; Bricelj, Aleša; Kohl, Franziska; Ng, Yuen Lam Dora; Monschke, Marius; Wagner, Karl G.; Krönke, Jan; Gütschow, Michael [MedChemComm, 2019, vol. 10, # 6, p. 1037 - 1041]

7
[ 430430-57-2 ]
[ 107-19-7 ]
[ 1333880-60-6 ]

Reference： [1]MedChemComm,2019,vol. 10,p. 1037 - 1041

8
[ 430430-57-2 ]
[ 702-24-9 ]
tert-butyl N-[2-[2-[2-[(4-methoxyphenyl)methylmethylamino]ethoxy]ethoxy]ethyl]carbamate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
44%	With potassium carbonate; In N,N-dimethyl-formamide; at 20℃; for 16h;	To a mixture of 2-[2-[2-(tert-butoxycarbonylamino)ethoxy]ethoxy]ethyl methanesulfonate (1.30 g, 3.97 mmol, synthesized via Step 1 of Intermediate AM) and 1-(4-methoxyphenyl)-N-methyl-methanamine (600 mg, 3.97 mmol) in DMF (15 mL) was added K2CO3 (1.10 g, 7.94 mmol). The reaction mixture was stirred at rt for 16 hours. On completion, the mixture was diluted with water (10 mL) and extracted with DCM (3×20 mL). The organic layers were dried over anhydrous Na2SO4, filtered and the filtrate was concentrated in vacuo to give a residue. The residue was purified by reverse phase chromatography (0.1% NH3.H2O) to give the title compound (670 mg, 44% yield) as a light yellow oil. LC-MS (ESI+) m/z 383.2 (M+H)+.

Reference： [1]Patent: US2019/192668,2019,A1 .Location in patent: Paragraph 2396; 2397

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[ CAS No. 430430-57-2 ] {[proInfo.proName]}

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Physicochemical Properties

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Application In Synthesis of [ 430430-57-2 ]

[ 430430-57-2 ] Synthesis Path-Upstream 1~1

[ 430430-57-2 ] Synthesis Path-Downstream 1~8

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