[ CAS No. 92159-87-0 ]

Name: 92159-87-0|Benzyl (4-bromophenyl)carbamate|98%
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SKU: A735019
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Quality Control of [ 92159-87-0 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 92159-87-0 ]

SDS Specification

Alternatived Products of [ 92159-87-0 ]

Product Details of [ 92159-87-0 ]

CAS No. :	92159-87-0	MDL No. :	MFCD01013385
Formula :	C₁₄H₁₂BrNO₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	OGIRMVQVHNCXEH-UHFFFAOYSA-N
M.W :	306.16 g/mol	Pubchem ID :	561232
Synonyms :

Calculated chemistry of [ 92159-87-0 ]

Physicochemical Properties

Num. heavy atoms :	18
Num. arom. heavy atoms :	12
Fraction Csp3 :	0.07
Num. rotatable bonds :	5
Num. H-bond acceptors :	2.0
Num. H-bond donors :	1.0
Molar Refractivity :	74.42
TPSA :	38.33 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	Yes
CYP2C9 inhibitor :	Yes
CYP2D6 inhibitor :	Yes
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-5.55 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.87
Log Po/w (XLOGP3) :	3.69
Log Po/w (WLOGP) :	3.86
Log Po/w (MLOGP) :	3.59
Log Po/w (SILICOS-IT) :	3.15
Consensus Log Po/w :	3.43

Druglikeness

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

Water Solubility

Log S (ESOL) :	-4.23
Solubility :	0.0182 mg/ml ; 0.0000594 mol/l
Class :	Moderately soluble
Log S (Ali) :	-4.19
Solubility :	0.02 mg/ml ; 0.0000653 mol/l
Class :	Moderately soluble
Log S (SILICOS-IT) :	-5.9
Solubility :	0.000387 mg/ml ; 0.00000126 mol/l
Class :	Moderately soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.24

Safety of [ 92159-87-0 ]

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

Application In Synthesis of [ 92159-87-0 ]

* 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 [ 92159-87-0 ]
Downstream synthetic route of [ 92159-87-0 ]

[ 92159-87-0 ] Synthesis Path-Upstream 1~1

1
[ 92159-87-0 ]
[ 375853-82-0 ]
[ 170011-57-1 ]

Reference： [1] Chemical Communications, 2017, vol. 54, # 1, p. 46 - 49

[ 92159-87-0 ] Synthesis Path-Downstream 1~10

1
[ 92159-87-0 ]
[ 133625-87-3 ]
(S)-4-[2-(4-amino-phenyl)-ethyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester [ No CAS ]
(S)-4-[2-(4-benzyloxycarbonylaminophenyl)ethyl]-3-(tert-butoxycarbonyl)-2,2-dimethyloxazolidine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: tert-butyl (4S)-2,2-dimethyl-4-vinyl-1,3-oxazolidine-3-carboxylate With 9-borabicyclo[3.3.1]nonane dimer In toluene at 80 - 85℃; Stage #2: benzyl (4-bromophenyl)carbamate With sodium hydroxide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; tetra-(n-butyl)ammonium iodide In toluene at 90℃; Further stages.;

Reference： [1]Sabat, Mark; Johnson, Carl R. [Organic Letters, 2000, vol. 2, # 8, p. 1089 - 1091]

2
[ 680596-79-6 ]
[ 92159-87-0 ]
[ 959939-45-8 ]

Yield	Reaction Conditions	Operation in experiment
72%	With potassium carbonate;tetrakis(triphenylphosphine) palladium(0); In N,N-dimethyl acetamide; water; at 80℃; for 24.0h;	Intermediate 37: Methyl 3-[4-[2-[5-f(4-fluorophenv0aminol-l,3,4-oxadiazol-2-yl1-lH- benzoimidazol-5-yllcvclohexylloxypropanoate; ) Benzyl N- [4-(l ,4-dioxaspiro [4.51 dec-7-en-8-vDphenyll carbamate; Tetrakistriphenylphosphine palladium (565 mg, 0.49 mmol) was added to a solution of 2- (l,4-dioxaspiro[4.5]dec-8-en-8-yl)-4,4,5,5-tetramethyl-l,3,2-dioxaborolane (1.3 g, 4.88 mmol) and benzyl N-(4-bromophenyl)carbamate (1.50 g, 4.88 mmol) in degassed DME (20 mL) and degassed 2M aqueous potassium carbonate solution (6.25 mL) and stirred under a nitrogen atmosphere at 80 0C for 24 h. The reaction mixture was cooled to ambient temperature and EtOAc (50 mL) was added before washing with water (2 x 20 mL) and brine (20 mL), dried (MgSO4) and concentrated in vacuo to leave a residue. The crude residue was purified by column chromatography, using a gradient of 20-70% EtOAc in isohexane as eluent, to give the title compound as a cream coloured solid (1.30 g, 72 %). 1H NMR delta 1.87-1.97 (2H, m), 2.42-2.5 (2H, m), 2.6-2.73 (2H, m), 4.03 (4H, s), 5.2 (2H, s), 5.9-5.99 (IH, m), 6.65 (IH, s), 7.5-7.7 (9H, m); MS m/e MH+ 266.

Reference： [1]Patent: WO2007/141517,2007,A1 .Location in patent: Page/Page column 77-78

3
[ 3422-03-5 ]
[ 5467-74-3 ]
[ 25203-36-5 ]
[ 92159-87-0 ]

Yield	Reaction Conditions	Operation in experiment
1: 62% 2: 13%	With copper(l) chloride In methanol at 20℃; for 3h;

Reference： [1]Moon, Soo-Yeon; Kim, U. Bin; Sung, Dan-Bi; Kim, Won-Suk [Journal of Organic Chemistry, 2015, vol. 80, # 3, p. 1856 - 1865]

4
[ 92159-87-0 ]
[ 60456-26-0 ]
(R)-3-(4-bromophenyl)-5-(hydroxymethyl)oxazolidin-2-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
76%		General procedure: Compound 2 (2 mmol) was dissolved in anhydrous THF (10 mL) then cooled to -78 C under nitrogen followed by slow addition of 1M LHMDS in THF solution (1.7 mL, 1.7 mmol) over 20 min. The resulting mixture was subsequently stirred at -78 C for 1 h before (R)-(-)-glycidyl butyrate (0.24 g, 1.7 mmol) was added drop wise at -78 C and the mixture was stirred at this temperature for 1 h then allowed to gradually warm to room temperature under stirring for 12 hrs. The reaction was quenched with DDW (10 mL) followed by EtOAc (4 mL). Then the two layers were separated and the aqueous layer was extracted with EtOAc (3×10 mL). The combined organic extracts were washed with saturated aqueous sodium chloride (3×5 mL), dried over Na2SO4, filtered, and concentrated under vacuum. The crude product was then dissolved in DCM (10 mL) and allowed to stand overnight to get a white precipitate which was filtered and washed with DCM.
65.6%		1.la (6.0 g, 19.6 mmol, 1.0 equiv) was dissolved in THE (60 mL) and cooled to -75 C. nBuLi (1 .51g, 23.5 mmol, 1.2 equiv) was gradually added and the reaction mixture was stirred at -75 C for 1 hour. (R)-oxiran-2-ylmethyl butyrate (2.82 g, 19.6 mmol, 1.0 equiv) was added, the reaction mixture was stirred at -75 C for 1 hour, allowed to attain room temperature, and stirred at room temperature overnight. The reaction mixture was quenched with saturated aqueous ammonium chloride solution and extracted with EtOAc. The organic layer was washed with brine, dried over sodium sulfate and concentrated. The residue was purified by silica gel column chromatography (50-60% EtOAc/Hexane) to afford product 1.lb (3.5 g, 65.6 % yield). LCMS (mlz): 274.1 [M+H]. 1H NMR(400 MHz, DMSO d6) 6 7.64 -7.49 (m, 4H), 5.23 (t, J = 5.7 Hz, 1H), 4.71 (td, J = 9.4, 3.7 Hz, 1H), 4.08 (t, J =9.0 Hz, 1H), 3.82 (dd, J= 8.8, 6.2 Hz, 1H), 3.68 (ddd, J 12.3, 5.5, 3.4 Hz, 1H), 3.56 (ddd, J = 12.3, 5.8, 4.1 Hz, 1H).

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2017,vol. 27,p. 5310 - 5321
[2]Journal of Medicinal Chemistry,2018,vol. 61,p. 9360 - 9370
[3]Patent: WO2015/66413,2015,A1 .Location in patent: Page/Page column 63; 64

5
[ 92159-87-0 ]
[ 183905-31-9 ]
[ 104392-69-0 ]

Yield	Reaction Conditions	Operation in experiment
	With lithium tert-butoxide; In tetrahydrofuran; methanol; N,N-dimethyl-formamide; at 0 - 20℃; for 16h;	To a solution of benzyl (4-bromophenyl)carbamate (10.0 g, 32.7 mmol) in the mixture of DMF (40 mL) and MeOH (2.6mL, 65.3 mmol) was added a solution of lithium 2- methylpropan-2-olate (7.8 g, 98.0 mmol) in THF (60 mL) at 0C, and then (S)-1-acetamido-3- chloropropan-2-yl acetate (12.6 g, 65.3 mmol) was added. The mixture was warmed to 20C andstirred for 16 hours. The mixture was concentrated to give a residue which was poured into ice- water (100 mL) and the solid was precipitated. The mixture was filtered, and the solid was washed with 100 mL of PE and dried in vacuum to give (S)-N-((3-(4-bromophenyl)-2- oxooxazolidin-5-yl)methyl)acetamide as a solid. MS (ESI) m/z:313.0[M+Hj.?H NMR (400MHz, DMSO-d6) oe 8.30 - 8.22 (m, 1H), 7.60 - 7.54 (m, 2H), 7.54 - 7.48 (m, 2H), 4.72 (dd,J= 6.0, 8.2 Hz, 1H), 4.10 (t, J= 8.9 Hz, 1H), 3.73 (dd, J= 6.6, 8.8 Hz, 1H), 3.41 (t, J= 5.4 Hz,2H), 1.83 (s, 3H).MS (ESI) m/z:313.0, 315.0 [M+Hj.

Reference： [1]Patent: WO2017/66964,2017,A1 .Location in patent: Page/Page column 48; 49

6
[ 92159-87-0 ]
[ 183905-31-9 ]
(S)-N-((3-(4-(5,6-dihydro-[1,2,4]triazolo[1,5-a]pyrazin-7(8H)-yl)phenyl)-2-oxooxazolidin-5-yl)methyl)acetamide [ No CAS ]

Reference： [1]Patent: WO2017/66964,2017,A1

7
[ 92159-87-0 ]
[ 375853-82-0 ]
[ 170011-57-1 ]

Reference： [1]Chemical Communications,2017,vol. 54,p. 46 - 49

8
[ 621-84-1 ]
[ 589-87-7 ]
[ 92159-87-0 ]

Yield	Reaction Conditions	Operation in experiment
90%	With copper(l) iodide; ethylenediamine; sodium t-butanolate In toluene at 100℃; for 5h;	2.2 General Procedure for the Synthesis of Alkyl Aryl Carbamates General procedure: CuI (10mol%) and EDA (10mol%) were added to a mixtureof O-alkyl carbamate (1mmol), NaOtBu (1.5mmol) and aryl halide (1mmol) in 2mL toluene and the mixture wasstirred for the appropriate time, which was determined byTLC monitoring, at 100°C. After completion of the reaction,the catalyst was removed by filtration and 20mL H2Owas added to the filtrate. The resultant mixture was extractedwith CHCl3.Then the organic phase was washed with water(2 × 10mL) and dried over anhydrous Na2SO4.After evaporationof CHCl3under reduced pressure, the correspondingcrude product was purified by flash chromatography to givethe desired pure cross-coupling product in good to excellentyield. In the case of using arylboronic acids as couplingpartners, Cu(OAc)2 was employed instead of CuI.

Reference： [1]Sardarian, Ali Reza; DindarlooInaloo, Iman; Zangiabadi, Milad [Catalysis Letters, 2018, vol. 148, # 2, p. 642 - 652]

9
[ 92159-87-0 ]
[ 389602-90-8 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: potassium carbonate / tetrakis(triphenylphosphine) palladium⁽⁰⁾ / N,N-dimethyl acetamide; water / 24 h / 80 °C 2: hydrogen / palladium 10% on activated carbon / tetrahydrofuran / 16 h / 20 °C

Reference： [1]Current Patent Assignee: ASTRAZENECA PLC - WO2007/141517, 2007, A1

10
[ 104-57-4 ]
[ 131818-17-2 ]
[ 92159-87-0 ]

Reference： [1]Organic and Biomolecular Chemistry,2019,vol. 17,p. 5891 - 5896

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[ CAS No. 92159-87-0 ]

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Product Details of [ 92159-87-0 ]

Calculated chemistry of [ 92159-87-0 ]

Physicochemical Properties

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Lipophilicity

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Water Solubility

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Application In Synthesis of [ 92159-87-0 ]

[ 92159-87-0 ] Synthesis Path-Upstream 1~1

[ 92159-87-0 ] Synthesis Path-Downstream 1~10

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