[ CAS No. 1333880-60-6 ]

Name: 1333880-60-6|tert-Butyl (2-(2-(2-(prop-2-yn-1-yloxy)ethoxy)ethoxy)ethyl)carbamate|95%
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Quality Control of [ 1333880-60-6 ]

COA NMR CNMR HPLC LC-MS

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Product Details of [ 1333880-60-6 ]

CAS No. :	1333880-60-6	MDL No. :	MFCD30534430
Formula :	C₁₄H₂₅NO₅	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	CC(C)(C)OC(=O)NCCOCCOCCOCC#C
M.W :	287.35 g/mol	Pubchem ID :	-
Synonyms :	1. T-BOc-n-amido-peg3-propargyl

Calculated chemistry of of [ 1333880-60-6 ]

Physicochemical Properties

Num. heavy atoms :	20
Num. arom. heavy atoms :	0
Fraction Csp3 :	0.79
Num. rotatable bonds :	13
Num. H-bond acceptors :	5.0
Num. H-bond donors :	1.0
Molar Refractivity :	75.34
TPSA :	66.02 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-7.63 cm/s

Lipophilicity

Log Po/w (iLOGP) :	3.88
Log Po/w (XLOGP3) :	0.6
Log Po/w (WLOGP) :	1.27
Log Po/w (MLOGP) :	0.61
Log Po/w (SILICOS-IT) :	2.09
Consensus Log Po/w :	1.69

Druglikeness

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

Water Solubility

Log S (ESOL) :	-1.14
Solubility :	20.7 mg/ml ; 0.0722 mol/l
Class :	Very soluble
Log S (Ali) :	-1.56
Solubility :	7.91 mg/ml ; 0.0275 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-2.96
Solubility :	0.312 mg/ml ; 0.00109 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	3.45

Safety of [ 1333880-60-6 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P264-P280-P302+P352-P337+P313-P305+P351+P338-P362+P364-P332+P313	UN#:	N/A
Hazard Statements:	H315-H319	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 1333880-60-6 ]

* 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 [ 1333880-60-6 ]

[ 1333880-60-6 ] Synthesis Path-Downstream 1~32

1
[ 1333880-60-6 ]
[ 1333880-63-9 ]

Reference： [1]Analytical Biochemistry,2011,vol. 417,p. 264 - 273

2
[ 1333880-60-6 ]
[ 1333880-67-3 ]

Reference： [1]Analytical Biochemistry,2011,vol. 417,p. 264 - 273

3
[ 1333880-60-6 ]
[ 1333880-69-5 ]

Reference： [1]Analytical Biochemistry,2011,vol. 417,p. 264 - 273

4
[ 1333880-60-6 ]
[ 35109-88-7 ]
[ 1333880-61-7 ]

Reference： [1]Analytical Biochemistry,2011,vol. 417,p. 264 - 273

5
[ 139115-92-7 ]
[ 106-96-7 ]
[ 1333880-60-6 ]

Yield	Reaction Conditions	Operation in experiment
72%	With tetra-(n-butyl)ammonium iodide; potassium iodide; potassium hydroxide; In tetrahydrofuran; at 25℃; for 16h;Inert atmosphere;	A mixture of <strong>[139115-92-7]tert-butyl N-[2-[2-(2-hydroxyethoxy)ethoxy]ethyl]carbamate</strong> (3.00 g, 12.0 mmol), 3-bromoprop-1-yne (1.72 g, 14.4 mmol, 1.24 mL), TBAI (356 mg, 962 umol), KI (299 mg, 1.81 mmol) and KOH (675 mg, 12.0 mmol) in THF (30 mL) was degassed and purged with N2 for 3 times, and then the mixture was stirred at 25 C. for 16 hrs under N2 atmosphere. On completion, the mixture was filtered and the filtrate was concentrated in vacuo. The residue was purified by silica gel chromatography to give the title compound (2.50 g, 72% yield) as light yellow oil. 1H NMR (400 MHz, CDCl3) delta 5.05 (s, 1H), 4.22 (d, J=2.4 Hz, 2H), 3.76-3.60 (m, 8H), 3.55 (t, J=5.2 Hz, 2H), 3.35-3.27 (m, 2H), 2.44 (t, J=2.4 Hz, 1H), 1.47 (s, 9H).
	With sodium hydroxide; In dichloromethane; at 50℃;	To a stirred solution of <strong>[139115-92-7]tert-butyl (2-(2-(2-hydroxyethoxy)ethoxy)ethyl)carbamate</strong> (0.854 g) in dichloromethane (20 mL) was added sodium hydroxide (0.5 g) and 3-bromoprop-1-yne (0.7 mL). The mixture was stirred at 50 C overnight, filtered through Celite and concentrated under reducedpressure to give the title compound.
	With sodium hydroxide; In dichloromethane; at 50℃;	To a stirred solution of <strong>[139115-92-7]tert-butyl (2-(2-(2-hydroxyethoxy)ethoxy)ethyl)carbamate</strong> (0.854 g) in dichloromethane (20 mL) was added sodium hydroxide (0.5 g) and 3-bromoprop-1-yne (0.7 mL). The mixture was stirred at 50 C. overnight, filtered through Celite and concentrated under reduced pressure to give the title compound.

1.1 g

With sodium hydride; In tetrahydrofuran; at 0 - 20℃; for 5h;

To a stirred solution of <strong>[139115-92-7]tert-butyl (2-(2-(2-hydroxyethoxy)ethoxy)ethyl)carbamate</strong> (1.0 g, 4.01 mmol, synthesized via Step 1 on Intermediate AC) in THF (50 ml) was added NaH (0.2 g, 4.81 mmol) at 0-5 C. 3-bromoprop-1-yne (0.9 ml, 6.02 mmol, CAS : 106-96-7) was added dropwise at 0-5 C. The reaction mixture was stirred at rt for 5 h. The resulting reaction mixture was poured into ice cold water (200 ml) and extracted with ethyl acetate (3×200 ml). The combined organic layer was dried over anhydrous Na2SO4, filtered and concentrated under vacuum to afford tert-butyl (2-(2-(2-(prop-2-yn-1-yloxy)ethoxy)ethoxy)ethyl)carbamate (1.1 g, 3.83 mmol). LCMS m/z (ES+): 188.2 (M-99)+.

Reference： [1]Patent: US2019/192668,2019,A1 .Location in patent: Paragraph 4042; 4043
[2]Analytical Biochemistry,2011,vol. 417,p. 264 - 273
[3]Patent: WO2017/214456,2017,A1 .Location in patent: Page/Page column 364
[4]Patent: US2019/153107,2019,A1 .Location in patent: Paragraph 1142
[5]Patent: US2019/192668,2019,A1 .Location in patent: Paragraph 2985; 2986

6
[ 139115-92-7 ]
[ 1333880-60-6 ]

Reference： [1]Bioscience, Biotechnology and Biochemistry,2016,vol. 80,p. 432 - 439
[2]MedChemComm,2019,vol. 10,p. 1037 - 1041

7
[ 107-19-7 ]
2-[2-(2-tert-butoxycarbonylaminoethoxy)ethoxy]ethyl bromide [ No CAS ]
[ 1333880-60-6 ]

Yield	Reaction Conditions	Operation in experiment
20%		10 mL of dry THF was added to a flask containing 2-propyn-1-ol (560 mg, 10 mmol) and NaH (480 mg, 20 mmol) and was stirred on ice for 20 min. After the addition of 6 (488 mg, 1.6 mmol) to the solution, it was stirred for an additional 2 h. An aqueous solution of NH4Cl was added to the reaction mixture to terminate the reaction, and the solution was then extracted with 60 mL of EtOAc. The organic layer was dried over Na2SO4. The resultant matter was purified by silica gel column chromatography (40 g, n-hexane-EtOAc 3/2) to yield 7 (90 mg, 0.31 mmol, 20%) as ayellow oil. 1H NMR (270 MHz, CDCl3): 5.00 (1H, br),4.18 (2H, d, J = 3.3 Hz), 3.70-3.66 (4H, m), 3.64-3.56 (4H, m), 3.50 (2H, t, J = 7.3 Hz), 3.28 (2H, t,J = 7.2 Hz), 2.40 (1H, t, J = 3.3 Hz), 1.41 (s, 9H); 13CNMR (67.8 MHz, CDCl3): 155.9, 79.5, 79.1, 74.5,70.4, 70.3, 70.19, 70.17, 69.0, 58.3, 40.3, 28.3; FD-MSm/z (rel.int.): 288 (100, [M + H]+), 287 (19.0, [M]+),69.0 (95.7), 57.0 (91.3); FD-HR-MS m/z: calcd. forC14H26NO5, 288.18110, found 288.18038.