[ CAS No. 33545-97-0 ] {[proInfo.proName]}

Name: 33545-97-0|N,N'-Di-Boc-1,4-butanediamine|95%
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SKU: A816495
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Quality Control of [ 33545-97-0 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 33545-97-0 ]

Product Details of [ 33545-97-0 ]

CAS No. :	33545-97-0	MDL No. :	MFCD21364426
Formula :	C₁₄H₂₈N₂O₄	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	OWOZLAYXMYQYNC-UHFFFAOYSA-N
M.W :	288.38	Pubchem ID :	11044423
Synonyms :

Calculated chemistry of [ 33545-97-0 ]

Physicochemical Properties

Num. heavy atoms :	20
Num. arom. heavy atoms :	0
Fraction Csp3 :	0.86
Num. rotatable bonds :	11
Num. H-bond acceptors :	4.0
Num. H-bond donors :	2.0
Molar Refractivity :	78.44
TPSA :	76.66 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) :	-6.39 cm/s

Lipophilicity

Log Po/w (iLOGP) :	3.35
Log Po/w (XLOGP3) :	2.35
Log Po/w (WLOGP) :	2.82
Log Po/w (MLOGP) :	1.83
Log Po/w (SILICOS-IT) :	1.62
Consensus Log Po/w :	2.39

Druglikeness

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

Water Solubility

Log S (ESOL) :	-2.38
Solubility :	1.2 mg/ml ; 0.00415 mol/l
Class :	Soluble
Log S (Ali) :	-3.6
Solubility :	0.0725 mg/ml ; 0.000251 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-3.4
Solubility :	0.116 mg/ml ; 0.000402 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.65

Safety of [ 33545-97-0 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P264-P270-P301+P312-P330	UN#:	N/A
Hazard Statements:	H302	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 33545-97-0 ]

* 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 [ 33545-97-0 ]
Downstream synthetic route of [ 33545-97-0 ]

[ 33545-97-0 ] Synthesis Path-Upstream 1~4

1
[ 33545-97-0 ]
[ 16011-97-5 ]

Reference： [1] Patent: US6337423, 2002, B1, . Location in patent: Example 1
[2] Bioorganic and Medicinal Chemistry Letters, 2013, vol. 23, # 24, p. 6656 - 6662

2
[ 33545-97-0 ]
[ 68076-36-8 ]

Reference： [1] Bioorganic and Medicinal Chemistry Letters, 2011, vol. 21, # 9, p. 2587 - 2590

3
[ 24424-99-5 ]
[ 110-60-1 ]
[ 68076-36-8 ]
[ 33545-97-0 ]

Reference： [1] Journal of Medicinal Chemistry, 2014, vol. 57, # 10, p. 4263 - 4272
[2] Bioorganic and Medicinal Chemistry, 2010, vol. 18, # 7, p. 2586 - 2597
[3] Synthetic Communications, 1990, vol. 20, # 16, p. 2559 - 2564
[4] Organic Letters, 2015, vol. 17, # 3, p. 422 - 425

4
[ 1070-19-5 ]
[ 110-60-1 ]
[ 68076-36-8 ]
[ 33545-97-0 ]

Reference： [1] Synthesis, 1982, # 5, p. 404 - 405

[ 33545-97-0 ] Synthesis Path-Downstream 1~23

1
[ 124-04-9 ]
[ 75-65-0 ]
[ 33545-97-0 ]

Reference： [1]Journal of the American Chemical Society,1972,vol. 94,p. 6203 - 6205
[2]Tetrahedron,1974,vol. 30,p. 2151 - 2157

2
[ 1070-19-5 ]
[ 110-60-1 ]
[ 68076-36-8 ]
[ 33545-97-0 ]

Reference： [1]Synthesis,1982,p. 404 - 405

3
[ 24424-99-5 ]
[ 110-60-1 ]
[ 68076-36-8 ]
[ 33545-97-0 ]

Reference： [1]Journal of Medicinal Chemistry,2014,vol. 57,p. 4263 - 4272
[2]Bioorganic and Medicinal Chemistry,2010,vol. 18,p. 2586 - 2597
[3]Synthetic Communications,1990,vol. 20,p. 2559 - 2564
[4]Organic Letters,2015,vol. 17,p. 422 - 425

4
[ 33545-97-0 ]
[ 36839-56-2 ]
4,9-diaza-1,12,15-trioxacycloheptadecane [ No CAS ]

Reference： [1]Journal of Heterocyclic Chemistry,1995,vol. 32,p. 1639 - 1640

5
[ 24424-99-5 ]
[ 110-60-1 ]
[ 33545-97-0 ]

Yield	Reaction Conditions	Operation in experiment
97%	In neat (no solvent); at 80℃; for 0.166667h;Green chemistry;	General procedure: The reactions were carried out in a 50 mL RB flask under reduced pressure for 10 min at 80C unless reported differently. In a typical experiment, 5 mmol of amine was added to 5 mmol of BOC anhydride, and the reaction was allowed to proceed for 10 min. The desired product was obtained in a rotary evaporator under vacuum conditions.
94.5%	With triethylamine; In dichloromethane; at 20℃; for 12h;Product distribution / selectivity;	1,4-Di(Boc-amino)-butane (Compound 63, Scheme 21) was prepared by adding Boc-anhydride (12 grams, 55 mmol) to a stirred solution of Compound 62 (1,4-diamino-butane, 2.2 grams, 25 mmol) and triethylamine (10.4 ml, 75 mmol) in CH2Cl2 (50 ml) at room temperature. After 12 hours, the reaction mixture was quenched with aqueous NH4Cl, extracted with CH2Cl2, and the combined organic layer was washed with 1% HCl, aqueous NaHCO3 and water, dried over MgSO4, and the solvents were removed under reduced pressure to afford Compound 63 as white solid (6.8 grams, 94.5% yield).1H NMR (500 MHz, CDCl3)-delta: 4.60 (bs, 2NH), 3.1 (s, 4H), 1.45-1.46 (m, 4H), 1.41 (s, 18H).
85.2%	With sodium hydrogencarbonate;	Commercially available putrescine 1 is (bis)-N-Boc protected to produce compound 2 (85.2% yield). Compound 2 is used to alkylate qty. 2 equivalents of propargyl bromide in the presence of sodium hydride producing compound 3 (59.5% yield). Yields in that transformation are further enhanced by using a mixture of dimethylformamide ("DMF") and tetrahydrofuran ("THF") in a ratio of 1:5. The propargyl groups in compound 3 are converted to the corresponding allenes in the presence of CuBr, formaldehyde, and diisopropylamine to yield intermediate compound 4 (38.7% yield). Compound 4 is de-protected in the presence of HCl to yield the desired target molecule MDL 72,527 (white solid, 65.8% yield). [00097] HPLC method of quantitation of MDL, natural polyamines and their acetyl derivatives in cell extracts as well as in human and animal serum is standardized. Therefore, the pharmacokinetics and pharmocodynamics of MDL 72,527 may be determined.

In 1,4-dioxane; for 25.5h;

The preparation of the known isocyanide intermediate (2) followed literature precedent: Xu et al. Synthesis2003, 1171. Briefly, 1, 4-diaminobutane (1, 4-DAB; 7.5 g, 85.08 mmol) was diluted in 30 mL of dioxane.Then, a solution of di-tert-butyldicarbonate (2.4 g, 11 mmol) in 30 mL of dioxane was then added dropwiseover 1.5 hours. This reaction was stirred for 24 hours and the solvent removed under vacuum. To thismixture, 50 mL of water was added and the resulting insoluble material was removed by filtration. Thefiltrate was extracted three times with 45 mL of DCM. The organic layers were dried with sodium sulfateand concentrated to give a 56-61% yield. Next, the product (2 mmol) was diluted in 5 mL DCM and formicacid (2 mmol) was added to the stirring reaction. The reaction was then placed into an ice-bath. Oncecooled, DIC (2 mmol) was added and the mixture stirred for 4 hours at room temperature. The reaction wasfiltered and the filtrate washed with saturated sodium bicarbonate. The organic layer was then dried withsodium sulfate and concentrated. The resulting product, tert-butyl (4-aminobutyl)-carbamate, was obtainedin 90-92% yield. This product (8.7 mmol) was then diluted with 13 mL of DCM, triethylamine (26.2 mmol)was added and the solution was cooled in an ice-bath. POCl3 (8.7 mmol) was then added dropwise. Thereaction was stirred for 30 minutes, followed by addition of potassium carbonate (8.7 mmol). The reactionwas then stirred for another 30 minutes and the aqueous layer extracted five times with DCM, the organiclayers combined, washed with water, dried with sodium sulfate, and concentrated. The final product waspurified by flash column chromatography (eluting at 50:50 ethylacetate: hexanes) giving a 72-76% yield.

Reference： [1]Tetrahedron Letters,2007,vol. 48,p. 8318 - 8322
[2]Research on Chemical Intermediates,2017,vol. 43,p. 1355 - 1363
[3]Patent: US2010/16610,2010,A1 .Location in patent: Page/Page column 35
[4]Patent: US6337423,2002,B1 .Location in patent: Example 1
[5]Chemical Communications,2015,vol. 51,p. 6504 - 6507
[6]Patent: WO2007/130589,2007,A2 .Location in patent: Page/Page column 22; Fig.19
[7]Journal of Heterocyclic Chemistry,1995,vol. 32,p. 1639 - 1640
[8]Bioorganic and Medicinal Chemistry Letters,2011,vol. 21,p. 2587 - 2590
[9]Bioorganic and Medicinal Chemistry Letters,2013,vol. 23,p. 6656 - 6662
[10]Organic and Biomolecular Chemistry,2018,vol. 16,p. 5580 - 5584

7
[ 33545-97-0 ]
[ 176039-38-6 ]
2-[N-(tert-butoxycarbonyl)-N-(tert-butoxycarbonyl-amino-4-n-butyl)-]amino 2-N-fluorenylmethoxycarbonylamino acetic acid [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2002,vol. 67,p. 5408 - 5411

8
[ 33545-97-0 ]
[ 106-96-7 ]
[ 836636-60-3 ]

Yield	Reaction Conditions	Operation in experiment
59.5%	With sodium hydride;	Commercially available putrescine 1 is (bis)-N-Boc protected to produce compound 2 (85.2% yield). Compound 2 is used to alkylate qty. 2 equivalents of propargyl bromide in the presence of sodium hydride producing compound 3 (59.5% yield). Yields in that transformation are further enhanced by using a mixture of dimethylformamide ("DMF") and tetrahydrofuran ("THF") in a ratio of 1:5. The propargyl groups in compound 3 are converted to the corresponding allenes in the presence of CuBr, formaldehyde, and diisopropylamine to yield intermediate compound 4 (38.7% yield). Compound 4 is de-protected in the presence of HCl to yield the desired target molecule MDL 72,527 (white solid, 65.8% yield). [00097] HPLC method of quantitation of MDL, natural polyamines and their acetyl derivatives in cell extracts as well as in human and animal serum is standardized. Therefore, the pharmacokinetics and pharmocodynamics of MDL 72,527 may be determined.
	With sodium hydride; In tetrahydrofuran; N,N-dimethyl-formamide;	Commercially available putrescine 1 is (bis)-N-Boc protected to produce compound 2 (85.2% yield). Compound 2 is used to alkylate qty. 2 equivalents of propargyl bromide in the presence of sodium hydride producing compound 3 (59.5% yield). Yields in that transformation are further enhanced by using a mixture of dimethylformamide ("DMF") and tetrahydrofuran ("THF") in a ratio of 1:5. The propargyl groups in compound 3 are converted to the corresponding allenes in the presence of CuBr, formaldehyde, and diisopropylamine to yield intermediate compound 4 (38.7% yield). Compound 4 is de-protected in the presence of HCl to yield the desired target molecule MDL 72,527 (white solid, 65.8% yield). [00097] HPLC method of quantitation of MDL, natural polyamines and their acetyl derivatives in cell extracts as well as in human and animal serum is standardized. Therefore, the pharmacokinetics and pharmocodynamics of MDL 72,527 may be determined.

Reference： [1]Patent: WO2007/130589,2007,A2 .Location in patent: Page/Page column 22; Fig.19
[2]Patent: WO2007/130589,2007,A2 .Location in patent: Page/Page column 22; Fig.19

9
[ 33545-97-0 ]
[ 16011-97-5 ]

Reference： [1]Patent: US6337423,2002,B1 .Location in patent: Example 1
[2]Bioorganic and Medicinal Chemistry Letters,2013,vol. 23,p. 6656 - 6662

10
[ 33545-97-0 ]
[ 129368-70-3 ]
[ 1047626-88-9 ]

Yield	Reaction Conditions	Operation in experiment
64%		6-(1,4-Di(boc-amino)-butane)-1-tert-butyldimethylsilyloxy hexane (Compound 64, Scheme 21) was prepared by adding NaH (0.75 grams, 19 mmol) to a stirred solution of Compound 63 (2.7 grams, 9.4 mmol) in DMF (30 ml) at room temperature. After 30 minutes additional portion of NaH, and Compound 61 (1.4 grams, 4.7 mmol) were added and the reaction mixture was stirred for 48 hours at room temperature. The reaction mixture was thereafter quenched with aqueous NH4Cl, extracted with ether, the combined organic layer was washed with brine, dried over MgSO4 and the solvents were removed under reduced pressure. The residue was purified by column chromatography using silica gel and 20-30% ethyl acetate in hexene as eluent to afford Compound 64 in the form of a colorless oil (1.5 grams, 64% yield).1H NMR (500 MHz, CDCl3)-delta: 4.61 (bs, NH), 3.58 (t, J=6 Hz, 2H), 3.13-3.10 (m, 6H), 1.55-1.45 (m, 8H), 1.42 (s, 18H), 1.35-1.22 (m, 4H), 0.87 (s, 9H), 0.03 (s, 6H);MS-(ESI), m/z: 503 MH+, 525 MNa+.

Reference： [1]Patent: US2010/16610,2010,A1 .Location in patent: Page/Page column 35

11
[ 24424-99-5 ]
[ 110-60-1 ]
di-tert-butyl butane-1,4-diyldicarbamate [ No CAS ]
[ 33545-97-0 ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine; In acetonitrile;	Reference Example 4 Synthesis of N,N'-diallyl-1,4-diaminobutane and Its Bis(dihydrogen phosphate) To 230 mL of acetonitrile, 20.0 g (227 mmol) of 1,4-diaminobutane and 63.3 mL (454 mmol) of triethylamine were dissolved, and 99.0 g (454 mmol) of di-tert-butyl dicarbonate was slowly added thereto with ice cooling with stirring. The resulting mixture was stirred at room temperature for 1 hour and cooled to -20 C. The precipitated solids were recovered by filtration and dried under reduced pressure to obtain 47.1 g of a crude product of tert-butyl butane-1,4-diyldicarbamate. This was dissolved to 300 mL of acetonitrile at 60 C. and left to stand at room temperature, thereby precipitating needle crystals. After cooling at -20 C., the crystals were recovered by filtration to obtain 45.6 g of di-tert-butyl butane-1,4-diyldicarbamate.

Reference： [1]Patent: US2010/189679,2010,A1

12
[ 33545-97-0 ]
C₃₇H₆₂N₆O₉ [ No CAS ]