[ CAS No. 146256-97-5 ] {[proInfo.proName]}

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Quality Control of [ 146256-97-5 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 146256-97-5 ]

Product Details of [ 146256-97-5 ]

CAS No. :	146256-97-5	MDL No. :	MFCD15142792
Formula :	C₁₄H₂₅NO₆	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	-
M.W :	303.35	Pubchem ID :	-
Synonyms :

Safety of [ 146256-97-5 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P280-P301+P312-P302+P352-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 146256-97-5 ]

* 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 [ 146256-97-5 ]
Downstream synthetic route of [ 146256-97-5 ]

[ 146256-97-5 ] Synthesis Path-Upstream 1~5

1
[ 146256-97-5 ]
[ 146256-98-6 ]

Reference： [1] Bioorganic and Medicinal Chemistry Letters, 2003, vol. 13, # 24, p. 4399 - 4403
[2] Patent: US2016/75708, 2016, A1, . Location in patent: Paragraph 0104; 0106
[3] Patent: KR2015/139962, 2015, A, . Location in patent: Paragraph 0155; 0158; 0161-0162

2
[ 146256-97-5 ]
[ 146256-98-6 ]
[ 170123-25-8 ]

Reference： [1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1993, # 12, p. 1313 - 1318

3
[ 146256-97-5 ]
[ 170123-25-8 ]

Yield	Reaction Conditions	Operation in experiment
41%	With potassium <i>tert</i>-butylate In toluene at -10 - 0℃; for 1.5 h; Inert atmosphere	To a suspension of potassium tert-butoxide (791 mg, 7.05 mmol) in anhydrous toluene (19 mL) at 10 C a solution of 30 (1.43 g, 4.7 mmol) in toluenewas added dropwise. The reactionwas stirred at 0 C for 90 min and then it was quenched with acetic acid (500 mL), followed by the addition of a cold solution of NaH2-PO4USDH2O (2.5 g) in 25 mL of water. The layers were separated, and the aqueous phase was extracted with CHCl3. The combined organic layers were dried over anhydrous Na2SO4 and concentrated under reduced pressure. The crude product was purified by flash chromatography (silica gel, pet. ether/EtOAc 5:1, Rf 0.44) obtaining the title compound 31 as a yellow oil (497 mg, 41percent yield). 1H NMR (CDCl3, 200 MHz) major rotamer: d 4.55 and 4.47 (s, 1H), 4.27-4.22 (m, 2H), 3.91-3.84 (m) and 3.82 (t, J = 8.2 Hz) 2H, 2.69 (t, J = 8.0 Hz, 2H), 1.49 and 1.43 (s, 9H), 1.30 (t, J = 7.1 Hz, 3H). Anal. C12H19NO5 (C, H, N).

Reference： [1] Chemical Communications, 2016, vol. 52, # 53, p. 8271 - 8274
[2] Journal of the Chemical Society - Perkin Transactions 1, 1997, # 15, p. 2179 - 2187
[3] Organic Letters, 2007, vol. 9, # 21, p. 4255 - 4258
[4] Tetrahedron Asymmetry, 2005, vol. 16, # 13, p. 2243 - 2247
[5] Bioorganic and Medicinal Chemistry Letters, 2008, vol. 18, # 6, p. 1931 - 1938
[6] European Journal of Medicinal Chemistry, 2012, vol. 56, p. 96 - 107
[7] Journal of the American Chemical Society, 2003, vol. 125, # 40, p. 12172 - 12178

4
[ 146256-97-5 ]
[ 146256-98-6 ]
[ 170123-25-8 ]

Reference： [1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1993, # 12, p. 1313 - 1318

5
[ 146256-97-5 ]
[ 101385-93-7 ]

Reference： [1] Bioorganic and Medicinal Chemistry Letters, 2003, vol. 13, # 24, p. 4399 - 4403

[ 146256-97-5 ] Synthesis Path-Downstream 1~4

2
[ 146256-97-5 ]
[ 146256-98-6 ]
[ 170123-25-8 ]

Reference： [1]Journal of the Chemical Society. Perkin transactions I,1993,p. 1313 - 1318

3
[ 146256-97-5 ]
[ 170123-25-8 ]

Yield	Reaction Conditions	Operation in experiment
41%	With potassium tert-butylate; In toluene; at -10 - 0℃; for 1.5h;Inert atmosphere;	To a suspension of potassium tert-butoxide (791 mg, 7.05 mmol) in anhydrous toluene (19 mL) at 10 C a solution of 30 (1.43 g, 4.7 mmol) in toluenewas added dropwise. The reactionwas stirred at 0 C for 90 min and then it was quenched with acetic acid (500 mL), followed by the addition of a cold solution of NaH2-PO4USDH2O (2.5 g) in 25 mL of water. The layers were separated, and the aqueous phase was extracted with CHCl3. The combined organic layers were dried over anhydrous Na2SO4 and concentrated under reduced pressure. The crude product was purified by flash chromatography (silica gel, pet. ether/EtOAc 5:1, Rf 0.44) obtaining the title compound 31 as a yellow oil (497 mg, 41% yield). 1H NMR (CDCl3, 200 MHz) major rotamer: d 4.55 and 4.47 (s, 1H), 4.27-4.22 (m, 2H), 3.91-3.84 (m) and 3.82 (t, J = 8.2 Hz) 2H, 2.69 (t, J = 8.0 Hz, 2H), 1.49 and 1.43 (s, 9H), 1.30 (t, J = 7.1 Hz, 3H). Anal. C12H19NO5 (C, H, N).

Reference： [1]Chemical Communications,2016,vol. 52,p. 8271 - 8274
[2]Journal of the Chemical Society. Perkin transactions I,1997,p. 2179 - 2187
[3]Organic Letters,2007,vol. 9,p. 4255 - 4258
[4]Tetrahedron Asymmetry,2005,vol. 16,p. 2243 - 2247
[5]Bioorganic and Medicinal Chemistry Letters,2008,vol. 18,p. 1931 - 1938
[6]European Journal of Medicinal Chemistry,2012,vol. 56,p. 96 - 107
[7]Journal of the American Chemical Society,2003,vol. 125,p. 12172 - 12178
[8]Organic Process Research and Development,2020,vol. 24,p. 792 - 801

4
[ 146256-97-5 ]
[ 146256-98-6 ]

Yield	Reaction Conditions	Operation in experiment
	With ethanol; sodium;Reflux;	The Preparation of Compound 14D: Sodium (27.6 g, 0.765 mol) was added stepwise to absolute ethanol (1.5 L). When the solid completely disappeared, compound 14C (300 g, 1.04 mol) was added to the solution. The reaction mixture was refluxed overnight, monitored with TCL (PE/EA=4:1), until the starting material was completely consumed. The reaction mixture was evaporated to remove most of the solvent. The residue was dissolved in water (1 L) and acidified with citric acid to pH 6. The mixture was extracted with EA (1 L×3). The extract liquors were combined, washed with brine (1 L×3), dried with anhydrous Na2SO4 and evaporated, to obtain compound 14D (169 g, 63.4percent) as a brown oily substance. The crude product was used directly in the next step without a further purification.
	With sodium ethanolate; In ethanol;Reflux;	Sodium ethoxide (27.6 g, 0.765 mol) was added stepwise to absolute ethanol (1.5 L). When the solid completely disappeared, compound 14C (300 g, 1.04 mol) was added to the solution. The reaction mixture was refluxed overnight, monitored with TCL (PE/EA=4:1), until the starting material was completely consumed. The reaction mixture was evaporated to remove most of the solvent. The residue was dissolved in water (1 L) and acidified with citric acid to pH 6. The mixture was extracted with EA (1 L×3). The extract liquors were combined, washed with brine (1 L×3), dried with anhydrous Na2SO4 and evaporated, to obtain compound 14D (169 g, 63.4percent) as a brown oily substance. The crude product was used directly in the next step without a further purification.

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2003,vol. 13,p. 4399 - 4403
[2]Patent: US2016/75708,2016,A1 .Location in patent: Paragraph 0104; 0106
[3]Patent: KR2015/139962,2015,A .Location in patent: Paragraph 0155; 0158; 0161-0162

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P342	If experiencing respiratory symptoms:
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P303 + P361 + P353	IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P304 + P312	IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell.
P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P304 + P341	IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P306 + P360	IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes.
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P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
P337 + P313	IF eye irritation persists: Get medical advice/attention.
P342 + P311	IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.
P370 + P376	In case of fire: Stop leak if safe to Do so.
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[ CAS No. 146256-97-5 ] {[proInfo.proName]}

Quality Control of [ 146256-97-5 ]

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Application In Synthesis of [ 146256-97-5 ]

[ 146256-97-5 ] Synthesis Path-Upstream 1~5

[ 146256-97-5 ] Synthesis Path-Downstream 1~4

Precautionary Statements-General

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