[ CAS No. 147353-95-5 ] {[proInfo.proName]}

Name: 147353-95-5|tert-Butyl (1-(4-chlorophenyl)-2-hydroxyethyl)carbamate|97%
Brand: Ambeed
SKU: A164407
Price: 76.0 USD
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Quality Control of [ 147353-95-5 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 147353-95-5 ]

Product Details of [ 147353-95-5 ]

CAS No. :	147353-95-5	MDL No. :	MFCD24387088
Formula :	C₁₃H₁₈ClNO₃	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	QUURCBFBLHSKLE-UHFFFAOYSA-N
M.W :	271.74	Pubchem ID :	19968645
Synonyms :

Calculated chemistry of [ 147353-95-5 ]

Physicochemical Properties

Num. heavy atoms :	18
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.46
Num. rotatable bonds :	6
Num. H-bond acceptors :	3.0
Num. H-bond donors :	2.0
Molar Refractivity :	70.94
TPSA :	58.56 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) :	-6.25 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.73
Log Po/w (XLOGP3) :	2.4
Log Po/w (WLOGP) :	2.57
Log Po/w (MLOGP) :	2.34
Log Po/w (SILICOS-IT) :	2.33
Consensus Log Po/w :	2.47

Druglikeness

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

Water Solubility

Log S (ESOL) :	-2.89
Solubility :	0.352 mg/ml ; 0.0013 mol/l
Class :	Soluble
Log S (Ali) :	-3.27
Solubility :	0.145 mg/ml ; 0.000535 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-3.84
Solubility :	0.039 mg/ml ; 0.000144 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	0.0
Synthetic accessibility :	2.57

Safety of [ 147353-95-5 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P280-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H319-H332-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 147353-95-5 ]

* 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 [ 147353-95-5 ]
Downstream synthetic route of [ 147353-95-5 ]

[ 147353-95-5 ] Synthesis Path-Upstream 1~2

1
[ 179811-64-4 ]
[ 24424-99-5 ]
[ 147353-95-5 ]

Yield	Reaction Conditions	Operation in experiment
88%	With triethylamine In tetrahydrofuran at 20℃;	Step 1: (rac)-tert-butyl (1 -(4-chlorophenyl)-2-hydroxyethyl)carbamate:To a solution of (rac)-2-amino-2-(4-chlorophenyl)ethanol (2 g, 1 1 .65 mmol) (prepared as described WO2009/47563 A1 ) in THF (20 ml) was added Boc anhydride (2.84 ml, 12.24 mmol) followed by triethylamine (2.436 ml, 17.48 mmol) . The reaction mixture was then stirred at RT and maintained at this temperature overnight. The reaction mixture was concentrated in vacuo, diluted with EtOAc and 1 N HCI and extracted. The organic extracts were then washed with brine, dried (Na2S04) and concentrated in vacuo affording the title compound as a sticky solid (2.8 g, 88percent). ¹H NMR (500 MHz, CDCI₃): 7.34 (2H, m), 7.27 (1 H, d), 5.35 (1 H, m), 4.75 (1 H, m), 3.75- 3.90 (2H, m), 1 .44 (9H, s).
14%	With triethylamine In methanol; ethyl acetate at 20℃; for 2 h;	The remainder of the solution was treated with triethylamine (18.02 mL, 129.31 mmol) and di-tert-butyl dicarbonate (14.11 g, 64.65 mmol). The mixture was stirred for 2 hours at room temperature before being partitioned between ethyl acetate and water. The organic layer was dried with magnesium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by MPLC on silica using gradient elution (10percent ethyl acetate / DCM to 50percent ethyl acetate / DCM). The desired product, tert-butyl l-(4- chlorophenyl)-2-hydroxyethylcarbamate (7.91 g, 45.0 percent), was thus isolated as a colourless solid. Impure fractions were repurified by MPLC to give a second crop (2.4 Ig, 14percent). IH NMR (399.9 MHz, DMSO-d6) δ 1.37 (9H, s), 3.41 - 3.52 (2H, m), 4.42 - 4.58 (IH, m), 4.79 (IH, t), 7.23 (IH, d), 7.31 (2H, d), 7.37 (2H, d).

Reference： [1] Patent: WO2012/69852, 2012, A1, . Location in patent: Page/Page column 137-138
[2] Patent: WO2009/47563, 2009, A1, . Location in patent: Page/Page column 99

2
[ 24424-99-5 ]
[ 6212-33-5 ]
[ 147353-95-5 ]

Reference： [1] Journal of Medicinal Chemistry, 2013, vol. 56, # 5, p. 2059 - 2073

[ 147353-95-5 ] Synthesis Path-Downstream 1~28

1
[ 147353-95-5 ]
[ 124-63-0 ]
[ 1143534-14-8 ]

Yield	Reaction Conditions	Operation in experiment
52.3%	With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 0 - 20℃; for 2.08333h;	Intermediate 23 : 2-(tert-butoxycarbonylamino)-2-(4-chlorophenvDethyl methanesulfonateMethanesulfonyl chloride (1.451 mL, 18.74 mmol) was added to tert-butyl l-(4- chlorophenyl)-2-hydroxyethylcarbamate (4.63 g, 17.04 mmol) and N,N- diisopropylethylamine (6.23 mL, 35.78 mmol) in DCM (40 mL) cooled to O0C over a period of 5 minutes under nitrogen. The resulting solution was stirred at 20 0C for 2 hours. The reaction mixture was diluted with DCM (100 mL) and washed sequentially with water <n="101"/>(100 mL). The organic layer was dried over MgSO4, filtered and evaporated to afford crude product. The crude product was purified by flash silica chromatography, elution gradient 0 to 10% EtOAc in DCM. Pure fractions were evaporated to dryness to afford 2- (tert-butoxycarbonylamino)-2-(4-chlorophenyl)ethyl methanesulfonate (3.12 g, 52.3 %) as a white solid. IH NMR (399.9 MHz, DMSO-d6) delta 1.39 (9H, s), 3.17 (3H, s), 4.22 - 4.28 (2H, m), 4.90 (IH, d), 7.40 - 7.46 (4H, m), 7.68 (IH, d). m/z (ESI+) (M-H)- = 348; HPLC tR = 2.32 min.

Reference： [1]Patent: WO2009/47563,2009,A1 .Location in patent: Page/Page column 98-99
[2]Journal of Medicinal Chemistry,2013,vol. 56,p. 2059 - 2073

2
[ 179811-64-4 ]
[ 24424-99-5 ]
[ 147353-95-5 ]

Yield	Reaction Conditions	Operation in experiment
88%	With triethylamine; In tetrahydrofuran; at 20℃;	Step 1: (rac)-tert-butyl (1 -(4-chlorophenyl)-2-hydroxyethyl)carbamate:To a solution of (rac)-2-amino-2-(4-chlorophenyl)ethanol (2 g, 1 1 .65 mmol) (prepared as described WO2009/47563 A1 ) in THF (20 ml) was added Boc anhydride (2.84 ml, 12.24 mmol) followed by triethylamine (2.436 ml, 17.48 mmol) . The reaction mixture was then stirred at RT and maintained at this temperature overnight. The reaction mixture was concentrated in vacuo, diluted with EtOAc and 1 N HCI and extracted. The organic extracts were then washed with brine, dried (Na2S04) and concentrated in vacuo affording the title compound as a sticky solid (2.8 g, 88%). 1H NMR (500 MHz, CDCI3): 7.34 (2H, m), 7.27 (1 H, d), 5.35 (1 H, m), 4.75 (1 H, m), 3.75- 3.90 (2H, m), 1 .44 (9H, s).
14 - 45%	With triethylamine; In methanol; ethyl acetate; at 20℃; for 2h;	The remainder of the solution was treated with triethylamine (18.02 mL, 129.31 mmol) and di-tert-butyl dicarbonate (14.11 g, 64.65 mmol). The mixture was stirred for 2 hours at room temperature before being partitioned between ethyl acetate and water. The organic layer was dried with magnesium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by MPLC on silica using gradient elution (10% ethyl acetate / DCM to 50% ethyl acetate / DCM). The desired product, tert-butyl l-(4- chlorophenyl)-2-hydroxyethylcarbamate (7.91 g, 45.0 %), was thus isolated as a colourless solid. Impure fractions were repurified by MPLC to give a second crop (2.4 Ig, 14%). IH NMR (399.9 MHz, DMSO-d6) delta 1.37 (9H, s), 3.41 - 3.52 (2H, m), 4.42 - 4.58 (IH, m), 4.79 (IH, t), 7.23 (IH, d), 7.31 (2H, d), 7.37 (2H, d).

Reference： [1]Patent: WO2012/69852,2012,A1 .Location in patent: Page/Page column 137-138
[2]Patent: WO2009/47563,2009,A1 .Location in patent: Page/Page column 99

3
[ 147353-95-5 ]
[ 73183-34-3 ]
[ 1378368-27-4 ]

Yield	Reaction Conditions	Operation in experiment
50%	With potassium acetate; 1,3-diisopropyl-1H-imidazol-3-ium chloride;palladium diacetate; In tetrahydrofuran; at 80℃; for 2h;Inert atmosphere;	Step 2: (rac)-tert-butyl (2-hydroxy-1-(4-(4,4,5,5-tetramethyl- 1,3,2-dioxaborolan-2- yl)phenyl)ethyl)carbamate:To a solution of (rac)-tert-butyl (1 -(4-chlorophenyl)-2-hydroxyethyl)carbamate (1 .7 g, 6.26 mmol) in THF (25 ml) was added bis(pinacolato)diboron (1 .747 g, 6.88 mmol), 1 ,3-di- isopropylimidazoliumchloride (0.160 g, 0.375 mmol) and potassium acetate (1 .535 g, 15.64 mmol). Nitrogen was bubbled through the reaction mixture for 10 min before the addition of palladium(ll)acetate (0.042 g, 0.188 mmol). The reaction mixture was then heated at 80 C for 2 h. The reaction mixture was cooled to room temperature, concentrated, diluted with EtOAc and water and extracted with EtOAc. The organic extracts were then washed with brine, dried (Na2S04), filtered and concentrated in vacuo. The resultant residue was purified by flash chromatography (0 to 50% EtOAc in cyclohexane), affording the title compound as a gummy solid (1 .13 g, 50%).LCMS (Method F): RT = 1 .32 min, (M-Boc) + H+ = 264.

Reference： [1]Patent: WO2012/69852,2012,A1 .Location in patent: Page/Page column 138

4
[ 147353-95-5 ]
(rac)-2-amino-2-(4-(4-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)pyrimidin-2-yl)phenyl)ethanol ditrifluoroacetate [ No CAS ]

Reference： [1]Patent: WO2012/69852,2012,A1

5
[ 147353-95-5 ]
[ 1378368-28-5 ]

Reference： [1]Patent: WO2012/69852,2012,A1

6
[ 147353-95-5 ]
(rac)-2-amino-2-(4-(4-(3-(tert-butyl)-4-isopropoxyphenyl)pyrimidin-2-yl)phenyl)ethanol ditrifluoroacetate [ No CAS ]

Reference： [1]Patent: WO2012/69852,2012,A1

7
[ 147353-95-5 ]
[ 1378368-30-9 ]

Reference： [1]Patent: WO2012/69852,2012,A1

8
[ 147353-95-5 ]
[ 1378365-65-1 ]

Reference： [1]Patent: WO2012/69852,2012,A1

9
[ 147353-95-5 ]
[ 1378368-32-1 ]

Reference： [1]Patent: WO2012/69852,2012,A1

10
[ 24424-99-5 ]
[ 6212-33-5 ]
[ 147353-95-5 ]