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[ CAS No. 147353-95-5 ]

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2D
Chemical Structure| 147353-95-5
Chemical Structure| 147353-95-5
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Product Details of [ 147353-95-5 ]

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

1. tert-Butyl (1-(4-chlorophenyl)-2-hydroxyethyl)carbamate

Computed Properties of [ 147353-95-5 ]

TPSA : 58.6 H-Bond Acceptor Count : 3
XLogP3 : 2.4 H-Bond Donor Count : 2
SP3 : 0.46 Rotatable Bond Count : 5

Safety of [ 147353-95-5 ]

Signal Word:WarningClassN/A
Precautionary Statements:P261-P280-P305+P351+P338UN#:N/A
Hazard Statements:H302-H315-H319-H332-H335Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 147353-95-5 ]

  • Upstream synthesis route of [ 147353-95-5 ]
  • Downstream synthetic route of [ 147353-95-5 ]

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

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YieldReaction ConditionsOperation 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 2.00 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
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Reference: [1] Journal of Medicinal Chemistry, 2013, vol. 56, # 5, p. 2059 - 2073
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