105580-41-4|tert-Butyl 4-acetylbenzoate| Ambeed

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Quality Control of [ 105580-41-4 ] Purity: 98% SDS Specification

COA

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Product Details of [ 105580-41-4 ]

CAS No. :	105580-41-4
Formula :	C₁₃H₁₆O₃
M.W :	220.26
SMILES Code :	O=C(OC(C)(C)C)C1=CC=C(C(C)=O)C=C1
MDL No. :	MFCD17676586
Boiling Point :	No data available
InChI Key :	QXQXBZLXIAUIBG-UHFFFAOYSA-N
Pubchem ID :	13844704

Safety of [ 105580-41-4 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H315-H319-H332-H335
Precautionary Statements:	P261-P280-P305+P351+P338

Computational Chemistry of [ 105580-41-4 ] Show Less

Physicochemical Properties

Num. heavy atoms	16
Num. arom. heavy atoms	6
Fraction Csp3	0.38
Num. rotatable bonds	4
Num. H-bond acceptors	3.0
Num. H-bond donors	0.0
Molar Refractivity	62.38
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	43.37 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	2.67
Log P_o/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry	2.92
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	2.84
Log P_o/w (MLOGP)? MLOGP: Topological method implemented from Moriguchi I. et al. 1992 Chem. Pharm. Bull. Moriguchi I. et al. 1994 Chem. Pharm. Bull. Lipinski PA. et al. 2001 Adv. Drug. Deliv. Rev.	2.43
Log P_o/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com	2.88
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	2.75

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-3.06
Solubility	0.192 mg/ml ; 0.000873 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble
Log S (Ali)? Ali: Topological method implemented from Ali J. et al. 2012 J. Chem. Inf. Model.	-3.49
Solubility	0.0709 mg/ml ; 0.000322 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com	-3.64
Solubility	0.0505 mg/ml ; 0.000229 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble

Pharmacokinetics

GI absorption? Gatrointestinal absorption: according to the white of the BOILED-Egg	High
BBB permeant? BBB permeation: according to the yolk of the BOILED-Egg	Yes
P-gp substrate? P-glycoprotein substrate: SVM model built on 1033 molecules (training set) and tested on 415 molecules (test set) 10-fold CV: ACC=0.72 / AUC=0.77 External: ACC=0.88 / AUC=0.94	No
CYP1A2 inhibitor? Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set) and tested on 3000 molecules (test set) 10-fold CV: ACC=0.83 / AUC=0.90 External: ACC=0.84 / AUC=0.91	Yes
CYP2C19 inhibitor? Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set) and tested on 3000 molecules (test set) 10-fold CV: ACC=0.80 / AUC=0.86 External: ACC=0.80 / AUC=0.87	Yes
CYP2C9 inhibitor? Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set) and tested on 2075 molecules (test set) 10-fold CV: ACC=0.78 / AUC=0.85 External: ACC=0.71 / AUC=0.81	No
CYP2D6 inhibitor? Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set) and tested on 1068 molecules (test set) 10-fold CV: ACC=0.79 / AUC=0.85 External: ACC=0.81 / AUC=0.87	No
CYP3A4 inhibitor? Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set) and tested on 2579 molecules (test set) 10-fold CV: ACC=0.77 / AUC=0.85 External: ACC=0.78 / AUC=0.86	No
Log Kp (skin permeation)? Skin permeation: QSPR model implemented from Potts RO and Guy RH. 1992 Pharm. Res.	-5.57 cm/s

Druglikeness

Lipinski? Lipinski (Pfizer) filter: implemented from Lipinski CA. et al. 2001 Adv. Drug Deliv. Rev. MW ≤ 500 MLOGP ≤ 4.15 N or O ≤ 10 NH or OH ≤ 5	0.0
Ghose? Ghose filter: implemented from Ghose AK. et al. 1999 J. Comb. Chem. 160 ≤ MW ≤ 480 -0.4 ≤ WLOGP ≤ 5.6 40 ≤ MR ≤ 130 20 ≤ atoms ≤ 70	None
Veber? Veber (GSK) filter: implemented from Veber DF. et al. 2002 J. Med. Chem. Rotatable bonds ≤ 10 TPSA ≤ 140	0.0
Egan? Egan (Pharmacia) filter: implemented from Egan WJ. et al. 2000 J. Med. Chem. WLOGP ≤ 5.88 TPSA ≤ 131.6	0.0
Muegge? Muegge (Bayer) filter: implemented from Muegge I. et al. 2001 J. Med. Chem. 200 ≤ MW ≤ 600 -2 ≤ XLOGP ≤ 5 TPSA ≤ 150 Num. rings ≤ 7 Num. carbon > 4 Num. heteroatoms > 1 Num. rotatable bonds ≤ 15 H-bond acc. ≤ 10 H-bond don. ≤ 5	0.0
Bioavailability Score? Abbott Bioavailability Score: Probability of F > 10% in rat implemented from Martin YC. 2005 J. Med. Chem.	0.55

Medicinal Chemistry

PAINS? Pan Assay Interference Structures: implemented from Baell JB. & Holloway GA. 2010 J. Med. Chem.	0.0 alert
Brenk? Structural Alert: implemented from Brenk R. et al. 2008 ChemMedChem	0.0 alert: heavy_metal
Leadlikeness? Leadlikeness: implemented from Teague SJ. 1999 Angew. Chem. Int. Ed. 250 ≤ MW ≤ 350 XLOGP ≤ 3.5 Num. rotatable bonds ≤ 7	No; 1 violation:MW<1.0
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) based on 1024 fragmental contributions (FP2) modulated by size and complexity penaties, trained on 12'782'590 molecules and tested on 40 external molecules (r² = 0.94)	1.57

Application In Synthesis of [ 105580-41-4 ]

* 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.

Downstream synthetic route of [ 105580-41-4 ]

[ 105580-41-4 ] Synthesis Path-Downstream 1~35

1
[ 6065-32-3 ]
[ 105580-41-4 ]
[ 130351-30-3 ]

References: [1]Journal of Medicinal Chemistry,1991,vol. 34,p. 555 - 560.

2
[ 867-13-0 ]
[ 105580-41-4 ]
ethyl 3-<4-(tert-butoxycarbonyl)phenyl>-3-methylacrylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
0.76 g (58%)	In tetrahydrofuran;	2) A solution of triethyl phosphonoacetate (0.98 ml) in anhydrous tetrahydrofuran (4 ml) is added dropwise to a solution of sodium hydride (60%, oily) (220 mg) in anhydrous tetrahydrofuran (15 ml) under a nitrogen atmosphere and ice cooling, and the mixture is stirred under ice cooling for 10 minutes. Then, a solution of <strong>[105580-41-4]t-butyl 4-acetylbenzoate</strong> (1.0 g) in anhydrous tetrahydrofuran (4 ml) is added dropwise to the mixture, stirring it at room temperature overnight. Ether is added to the reaction mixture under ice cooling, and the whole is extracted. The organic layer is washed with a 10% aqueous citric acid solution, water and saturated brine successively, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue is purified by silica gel column chromatography to give 0.76 g (58%) of ethyl 4-(t-butoxycarbonyl)-beta-methylcinnamate. IR (Film, cm-1) 2979, 2934, 1713, 1631, 1567, 1455, 1169, 1115

References: [1]Chemical and Pharmaceutical Bulletin,1995,vol. 43,p. 829 - 841.
[2]Patent: US6329547,2001,B1 .

3
[ 105580-41-4 ]
[ 149325-57-5 ]

References: [1]Chemical and Pharmaceutical Bulletin,1995,vol. 43,p. 829 - 841.

4
[ 105580-41-4 ]
tert-butyl 4-(3-bromo-1-methylpropyl)benzoate [ No CAS ]

References: [1]Chemical and Pharmaceutical Bulletin,1995,vol. 43,p. 829 - 841.

5
[ 105580-41-4 ]
[ 149324-79-8 ]

References: [1]Chemical and Pharmaceutical Bulletin,1995,vol. 43,p. 829 - 841.

6
[ 105580-41-4 ]
[ 170799-76-5 ]

References: [1]Chemical and Pharmaceutical Bulletin,1995,vol. 43,p. 829 - 841.

7
[ 105580-41-4 ]
[ 170799-79-8 ]

References: [1]Chemical and Pharmaceutical Bulletin,1995,vol. 43,p. 829 - 841.

8
[ 105580-41-4 ]
[ 170799-74-3 ]

References: [1]Chemical and Pharmaceutical Bulletin,1995,vol. 43,p. 829 - 841.

9
[ 105580-41-4 ]
tert-butyl 4-<3-(2-cyano-3-oxocyclopentanyl)-1-methylpropyl>benzoate [ No CAS ]

References: [1]Chemical and Pharmaceutical Bulletin,1995,vol. 43,p. 829 - 841.

10
[ 105580-41-4 ]
[ 149325-60-0 ]

References: [1]Chemical and Pharmaceutical Bulletin,1995,vol. 43,p. 829 - 841.

11
[ 105580-41-4 ]
[ 149325-61-1 ]

References: [1]Chemical and Pharmaceutical Bulletin,1995,vol. 43,p. 829 - 841.

12
[ 105580-41-4 ]
[ 170799-58-3 ]

References: [1]Chemical and Pharmaceutical Bulletin,1995,vol. 43,p. 829 - 841.

13
[ 105580-41-4 ]
N-<4-<3-(2,4-diamino-6,7-dihydro-5H-cyclopenta<d>pyrimidin-5-yl)-1-methylpropyl>benzoyl>-L-glutamic acid [ No CAS ]

References: [1]Chemical and Pharmaceutical Bulletin,1995,vol. 43,p. 829 - 841.

14
[ 105580-41-4 ]
[ 1054687-13-6 ]

References: [1]Chemical and Pharmaceutical Bulletin,1995,vol. 43,p. 829 - 841.

15
[ 105580-41-4 ]
[ 125991-45-9 ]

References: [1]Journal of Medicinal Chemistry,1991,vol. 34,p. 555 - 560.

16
[ 105580-41-4 ]
[ 125991-46-0 ]

References: [1]Journal of Medicinal Chemistry,1991,vol. 34,p. 555 - 560.

17
[ 105580-41-4 ]
[ 125991-47-1 ]

References: [1]Journal of Medicinal Chemistry,1991,vol. 34,p. 555 - 560.

18
[ 105580-41-4 ]
4-[3-(2,4-Diamino-6,7-dihydro-5H-pyrrolo[2,3-d]pyrimidin-5-yl)-1-methyl-propyl]-benzoic acid [ No CAS ]

References: [1]Journal of Medicinal Chemistry,1991,vol. 34,p. 555 - 560.

19
[ 105580-41-4 ]
4-[3-(2,4-Diamino-7H-pyrrolo[2,3-d]pyrimidin-5-yl)-1-methyl-propyl]-benzoic acid [ No CAS ]

References: [1]Journal of Medicinal Chemistry,1991,vol. 34,p. 555 - 560.

20
[ 105580-41-4 ]
[ 125991-61-9 ]

References: [1]Journal of Medicinal Chemistry,1991,vol. 34,p. 555 - 560.

21
[ 105580-41-4 ]
[ 130377-73-0 ]

References: [1]Journal of Medicinal Chemistry,1991,vol. 34,p. 555 - 560.

22
[ 105580-41-4 ]
[ 130377-72-9 ]

References: [1]Journal of Medicinal Chemistry,1991,vol. 34,p. 555 - 560.

23
[ 105580-41-4 ]
[ 125991-66-4 ]

References: [1]Journal of Medicinal Chemistry,1991,vol. 34,p. 555 - 560.

24
[ 105580-41-4 ]
[ 125991-64-2 ]

References: [1]Journal of Medicinal Chemistry,1991,vol. 34,p. 555 - 560.

25
[ 105580-41-4 ]
[ 125991-65-3 ]

References: [1]Journal of Medicinal Chemistry,1991,vol. 34,p. 555 - 560.

26
[ 105580-41-4 ]
[ 125991-63-1 ]

References: [1]Journal of Medicinal Chemistry,1991,vol. 34,p. 555 - 560.

27
[ 105580-41-4 ]
[ 80459-44-5 ]
sodium (1Z,3E)-1-methyl-1-(4-t-butoxycarbonylphenyl)-2-methoxy-carbonyl-4-(3-methoxyphenyl)butadiene-3-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
37%		(4) The compound (10.0 g) obtained in (2) above and the compound (8.33 g) obtained in (1) above are dissolved in 55 ml of tert-butyl alcohol.. To the solution, a solution of 4.67 g of potassium tert-butoxide in tert-butyl alcohol (40 ml) is added dropwise (under nitrogen atmosphere, ice-cooling, internal temperature of 21-23C), which is followed by stirring for 2 hours at 20 C. To the reaction solution is added 0.87 ml of acetic acid, and the mixture is concentrated under reduced pressure.. The residue is mixed with toluene, subjected to azeotropic evaporation, and the residue is re-dissolved in 100 ml of toluene.. To the solution is added 1.69 g of potassium tert-butoxide under ice-cooling, and stirred for 1 hour at 20 C. After addition of 2.8 ml of acetic acid, the organic layer is washed with brine, 1 M hydrochloric acid, water and brine, successively, dried over magnesium sulfate and concentrated under reduced pressure.. The residue is dissolved in 200 ml of diisopropyl ether.. To the solution is added dropwise 5.1 g of 28 % sodium methoxide solution in methanol under ice-cooling, and stirred at room temperature overnight.. The precipitated crystals are collected by filtration, washed with diisopropyl ether and air-dried (50 C) to give sodium (1Z, 3E)-1-methyl-1-(4-t-butoxycarbonylphenyl)-2-methoxy-carbonyl-4-(3-methoxyphenyl)butadiene-3-carboxylate (yield 6.58 g, 37 %). MP. > 196 C (decomp.)

References: [1]Patent: EP1403252,2004,A1 .Location in patent: Page 8-9.

28
[ 79-37-8 ]
[ 586-89-0 ]
[ 105580-41-4 ]

Yield	Reaction Conditions	Operation in experiment
69%		(1) 4-Acetylbenzoic acid (100 g) is suspended into 500 ml of dichloromethane.. To the suspension are added 64 ml of oxalyl chloride and 4.7 ml of N,N-dimethylformamide at room temperature, and the mixture is stirred for 2 hours at room temperature.. The reaction solution is concentrated under reduced pressure and the residue is dissolved by adding 250 ml of chloroform and 175 ml of tert-butyl alcohol.. To the solution is then added dropwise 156 ml of pyridine under ice-cooling (12C).. The reaction mixture is stirred for 30 minutes at room temperature and concentrated under reduced pressure.. The residue is dissolved in toluene and the solution is washed with 2M hydrochloric acid, saturated aqueous sodium hydrogen carbonate solution and brine, successively.. The organic layer is dried over sodium sulfate and concentrated under reduced pressure.. hexane is added to the residue and the mixture is stirred under ice-cooling.. The precipitated crystals are collected by filtration, washed with cold hexane and dried in vacuo to give tert-butyl 4-acetylbenzoate (yield 96.82 g, 69 %). M.p. 59-60 C

References: [1]Patent: EP1403252,2004,A1 .Location in patent: Page 8.

29
[ 37746-78-4 ]
[ 105580-41-4 ]
[ 125991-45-9 ]

Yield	Reaction Conditions	Operation in experiment
	With iodine; In benzene-ether-tetrahydrofuran; water;	REFERENCE EXAMPLE 17 Production of ethyl 5-[4-(tert-butoxycarbonyl)-phenyl]hexanoate: In a solution of <strong>[105580-41-4]ter<strong>[105580-41-4]t-butyl 4-acetylbenzoate</strong></strong> (19.90 g) in a benzene-ether-tetrahydrofuran mixture (3:3:2, 200 ml) was suspended zinc (11.81 g), to which ethyl 4-bromocrotonate (17.44 g) was added slowly while heating and stirring, and then iodine (about 20 mg) was added. The resulting mixture was refluxed by heating on an oil bath (60-70 C.) for 1 hour, then ethyl 4-bromocrotonate (3.00 g) was added, and the mixture was further refluxed by heating for 15 minutes. After cooling to room temperature, the reaction mixture was added to water (500 ml), adjusted to pH 4.9 by addition of acetic acid and extracted with ether. The extract was washed with 5% aqueous ammonia and dried with anhydrous magnesium sulfate. The residue obtained by evaporation of the solvent under reduced pressure was purified by column chromatography (carrier; silica gel, 300 g, developing solvent; ethyl acetate-hexane=1:5), to give the object compound. IR (Neat): 3480, 2975, 1720, 1700, 1650, 1605 cm-1. 1 H--NMR (CDCl3) delta: 1.20 (3H,t,J=7Hz), 1.53 (12H,s), 2.64 (2H,d,J=7Hz), 2.67 (1H,brs),3.63 (3H,s), 4.08 (2H,q,J=7Hz), 5.80 (1H,d,J=15Hz), 6.80 (1H,dt,J=15Hz,7Hz), 7.45 (2H,d,J=8Hz), 7.90 (2H,d,J=8Hz).

References: [1]Patent: US4997838,1991,A .

30
[ 1117-71-1 ]
[ 105580-41-4 ]
5-[4-(tert-butoxycarbonyl)phenyl]-5-hydroxy-2-hexenoic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With iodine; In benzene-ether-tetrahydrofuran;	Reference Example 14 Production of 5-[4-(tert-butoxycarbonyl)phenyl]-5-hydroxy-2-hexenoic acid: To a suspension obtained by adding a solution of <strong>[105580-41-4]4-acetylbenzoic acid tert-butyl ester</strong> (7.82 g) in benzene-ether-tetrahydrofuran (3:3:2, 80 ml) to 4.64 g (71 mmol) of zinc, were added gradually under heating and stirring 4-bromocrotonic acid methyl ester (6.36 g) and iodine (20 mg). After reflux under heating in an oil bath at 70 C. for 1 hour, methyl 4-bromocrotonate (2.13 g) and zinc (1.55 g) were added, followed by reflux under heating for 30 minutes. The temperature was cooled down to room temperature, and the reaction mixture was poured into water (300 ml) and adjusted to pH 5 with acetic acid. The organic layer obtained by extraction with ether was washed with 5% aqueous ammonia and then dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure and the resulting residue was purified by column chromatography (support; silica gel, 200 g, developing agent; ethyl acetate:hexane=1:4), to obtain the object compound (9.2 g). IR (Neat): 3480, 2975, 1720, 1700, 1650, 1605 cm-1 1 H-NMR (CDCl3) delta: 1.53 (12H,s), 2.64 (2H,d,j=7Hz), 2.67 (1H,brs), 3.63 (3H,s), 5.80 (1H,d,j=15Hz), 6.80 (1H,dt, j=15Hz,7Hz), 7.45 (2H,d,j=8Hz), 7.90 (2H,d,j=8Hz).

References: [1]Patent: US4946846,1990,A .

Yield	Reaction Conditions	Operation in experiment
		Alternatively, 4-(t-butoxycarbonyl)acetophenone can be isolated by distillation under reduced pressure, bp 90-100 C./0.1 mm.

32
[ 105580-41-4 ]
[ 945401-49-0 ]

Yield	Reaction Conditions	Operation in experiment
	With pyridine; selenium(IV) oxide; at 90℃; for 6h;	4-Oxalyl-benzoic acid tert-butyl ester. To solution of 4-acetyl-benzoic acid tert-butyl ester (6.0 g, 27.2 mmol) in pyridine (1000 mL) at 90 0C was added selenium dioxide (5.29 g, 47.7 mmol) portionwise over 2h. After 4 h, the reaction mixture was cooled to RT and filtered via Celite. The solvent was removed in vacuo. The residue was diluted with EtOAc, washed with 0.5N HCl, dried (MgSO4), filtered, and concentrated in vacuo. The material was used without further purification. 1H NMR (CDCl3) delta 8.39 (d, J = 8.1 Hz, 2H), 8.11 (d, J = 8.1 Hz, 2H), 1.61 (s, 9H).

References: [1]Patent: WO2007/87130,2007,A2 .Location in patent: Page/Page column 57.

33
[ 31076-84-3 ]
[ 75-65-0 ]
[ 105580-41-4 ]

Yield	Reaction Conditions	Operation in experiment
	With pyridine; dmap; for 18h;	4-Acetyl-benzoic acid tert-butyl ester. To a slurry of 4-acetyl-benzoic acid (21.3 g, 130 mmol) inCH2Cl2 (200 mL) at RT was added oxalyl chloride (11.93 mL, 136 mmol), and then catalytic DMF (0.7 mL) was added drop wise. After Ih, the solvent was removed from the resultant solution. The solid was dissolved in CH2Cl2 and washed with 0.5 N HCl and H2O. The combined organic extracts were washed with brine, dried over MgSOpsi filtered, and concentrated in vacuo. The solid was dissolved in pyridine (100 mL) and to the solution was added DMAP (0.793 g, 6.49 mmol) and t-butyl alcohol (31.0 mL, 324 mmol). After 18h, the solvent was removed. The residue was dissolved in EtOAc, washed with IN HCl, 0.5 N NaOH, dried over MgSOphi filtered, and concentrated in vacuo. The solid was used without further <n="58"/>purification.1HNMR (CDCl3) delta 8.06 (d, J= 8.1 Hz, 2H), 7.97 (d, J= 8.1 Hz, 2H)5 2.63 (s, 3H), 1.60 (s, 9H). cal'd 221 (MH+), exp 221 (MH+).

References: [1]Patent: WO2007/87130,2007,A2 .Location in patent: Page/Page column 56-57.

34
[ 1779-49-3 ]
[ 105580-41-4 ]
[ 117347-38-3 ]

Yield	Reaction Conditions	Operation in experiment
52%		Methyl triphenylphosponium bromide (15.3 g) was suspended in THF (100 ml_) at 0 0C. n-Butyllithium (25.6 mL of a 1.6 M solution in hexanes) was added dropwise at 0 0C. The yellow solution was stirred at 0 0C (1 h). The ketone (4.7 g, 21.4 mmol) was added, and the resulting slurry was stirred at 25 0C (18 h). The mixture was quenched with water, and the mixture was extracted with Et2O. The combined Et2O layers were washed with brine and dried (MgSO4). The mixture was filtered and concentrated. The residue was filtered through a plug of SiO2 (rinsing with CH2CI2). The solution was concentrated. The residue was purified via gradient flash chromatography (5/1 hexanes/EtOAc, SiO2) which furnished 2.45 g (52 %) of the alkene as a colorless oil.

References: [1]Patent: WO2009/5671,2009,A2 .Location in patent: Page/Page column 123.

35
[ 586-89-0 ]
[ 36805-97-7 ]
[ 105580-41-4 ]

Yield	Reaction Conditions	Operation in experiment
35%	In toluene; at 85℃; for 19h;	The carboxylic acid (10 g, 60.9 mmol) and Me2NCH(OtBu)2 (25 g) were heated in toluene (300 ml_) for 5 hours (85 0C). More Me2NCH(OtBu)2 (25 g) was added, and the reaction was heated at 85 0C for 14 hours. The solution was partitioned between EtOAc and sat. NaHCO3(aq.). The aqueous layer was extracted with EtOAc. The combined organic layers were washed with brine and dried over MgSO4. The solution residue was filtered through a plug of SiO2 rinsing with CH2CI2. This afforded 4.7 g (35 %) of the tert-butyl ester as a solid.

References: [1]Patent: WO2009/5671,2009,A2 .Location in patent: Page/Page column 122-123.

Historical Records

Technical Information

• Acyl Group Substitution • Baeyer-Villiger Oxidation • Barbier Coupling Reaction • Baylis-Hillman Reaction • Benzylic Oxidation • Birch Reduction • Blanc Chloromethylation • Bouveault-Blanc Reduction • Bucherer-Bergs Reaction • Catalytic Hydrogenation • Clemmensen Reduction • Complex Metal Hydride Reductions • Corey-Bakshi-Shibata (CBS) Reduction • Corey-Chaykovsky Reaction • Ester Cleavage • Fischer Indole Synthesis • Friedel-Crafts Reaction • Grignard Reaction • Henry Nitroaldol Reaction • Horner-Wadsworth-Emmons Reaction • Hydride Reductions • Hydrogenolysis of Benzyl Ether • Lawesson's Reagent • Leuckart-Wallach Reaction • McMurry Coupling • Meerwein-Ponndorf-Verley Reduction • Passerini Reaction • Paternò-Büchi Reaction • Petasis Reaction • Peterson Olefination • Pictet-Spengler Tetrahydroisoquinoline Synthesis • Preparation of Aldehydes and Ketones • Preparation of Alkylbenzene • Preparation of Amines • Prins Reaction • Reactions of Aldehydes and Ketones • Reactions of Amines • Reactions of Benzene and Substituted Benzenes • Reactions with Organometallic Reagents • Reformatsky Reaction • Robinson Annulation • Schlosser Modification of the Wittig Reaction • Schmidt Reaction • Specialized Acylation Reagents-Carbodiimides and Related Reagents • Specialized Acylation Reagents-Ketenes • Stobbe Condensation • Tebbe Olefination • Ugi Reaction • Vilsmeier-Haack Reaction • Wittig Reaction • Wolff-Kishner Reduction

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[ 105580-41-4 ]

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Precautionary Statements-General
Code	Phrase
P101	If medical advice is needed,have product container or label at hand.
P102	Keep out of reach of children.
P103	Read label before use
Prevention
Code	Phrase
P201	Obtain special instructions before use.
P202	Do not handle until all safety precautions have been read and understood.
P210	Keep away from heat/sparks/open flames/hot surfaces. - No smoking.
P211	Do not spray on an open flame or other ignition source.
P220	Keep/Store away from clothing/combustible materials.
P221	Take any precaution to avoid mixing with combustibles
P222	Do not allow contact with air.
P223	Keep away from any possible contact with water, because of violent reaction and possible flash fire.
P230	Keep wetted
P231	Handle under inert gas.
P232	Protect from moisture.
P233	Keep container tightly closed.
P234	Keep only in original container.
P235	Keep cool
P240	Ground/bond container and receiving equipment.
P241	Use explosion-proof electrical/ventilating/lighting/equipment.
P242	Use only non-sparking tools.
P243	Take precautionary measures against static discharge.
P244	Keep reduction valves free from grease and oil.
P250	Do not subject to grinding/shock/friction.
P251	Pressurized container: Do not pierce or burn, even after use.
P260	Do not breathe dust/fume/gas/mist/vapours/spray.
P261	Avoid breathing dust/fume/gas/mist/vapours/spray.
P262	Do not get in eyes, on skin, or on clothing.
P263	Avoid contact during pregnancy/while nursing.
P264	Wash hands thoroughly after handling.
P265	Wash skin thouroughly after handling.
P270	Do not eat, drink or smoke when using this product.
P271	Use only outdoors or in a well-ventilated area.
P272	Contaminated work clothing should not be allowed out of the workplace.
P273	Avoid release to the environment.
P280	Wear protective gloves/protective clothing/eye protection/face protection.
P281	Use personal protective equipment as required.
P282	Wear cold insulating gloves/face shield/eye protection.
P283	Wear fire/flame resistant/retardant clothing.
P284	Wear respiratory protection.
P285	In case of inadequate ventilation wear respiratory protection.
P231 + P232	Handle under inert gas. Protect from moisture.
P235 + P410	Keep cool. Protect from sunlight.
Response
Code	Phrase
P301	IF SWALLOWED:
P304	IF INHALED:
P305	IF IN EYES:
P306	IF ON CLOTHING:
P307	IF exposed:
P308	IF exposed or concerned:
P309	IF exposed or if you feel unwell:
P310	Immediately call a POISON CENTER or doctor/physician.
P311	Call a POISON CENTER or doctor/physician.
P312	Call a POISON CENTER or doctor/physician if you feel unwell.
P313	Get medical advice/attention.
P314	Get medical advice/attention if you feel unwell.
P315	Get immediate medical advice/attention.
P320
P302 + P352	IF ON SKIN: wash with plenty of soap and water.
P321
P322
P330	Rinse mouth.
P331	Do NOT induce vomiting.
P332	IF SKIN irritation occurs:
P333	If skin irritation or rash occurs:
P334	Immerse in cool water/wrap n wet bandages.
P335	Brush off loose particles from skin.
P336	Thaw frosted parts with lukewarm water. Do not rub affected area.
P337	If eye irritation persists:
P338	Remove contact lenses, if present and easy to do. Continue rinsing.
P340	Remove victim to fresh air and keep at rest in a position comfortable for breathing.
P341	If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P342	If experiencing respiratory symptoms:
P350	Gently wash with plenty of soap and water.
P351	Rinse cautiously with water for several minutes.
P352	Wash with plenty of soap and water.
P353	Rinse skin with water/shower.
P360	Rinse immediately contaminated clothing and skin with plenty of water before removing clothes.
P361	Remove/Take off immediately all contaminated clothing.
P362	Take off contaminated clothing and wash before reuse.
P363	Wash contaminated clothing before reuse.
P370	In case of fire:
P371	In case of major fire and large quantities:
P372	Explosion risk in case of fire.
P373	DO NOT fight fire when fire reaches explosives.
P374	Fight fire with normal precautions from a reasonable distance.
P376	Stop leak if safe to do so. Oxidising gases (section 2.4) 1
P377	Leaking gas fire: Do not extinguish, unless leak can be stopped safely.
P378
P380	Evacuate area.
P381	Eliminate all ignition sources if safe to do so.
P390	Absorb spillage to prevent material damage.
P391	Collect spillage. Hazardous to the aquatic environment
P301 + P310	IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.
P301 + P312	IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P301 + P330 + P331	IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.
P302 + P334	IF ON SKIN: Immerse in cool water/wrap in wet bandages.
P302 + P350	IF ON SKIN: Gently wash with plenty of soap and water.
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.
P307 + P311	IF exposed: call a POISON CENTER or doctor/physician.
P308 + P313	IF exposed or concerned: Get medical advice/attention.
P309 + P311	IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician.
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.
P370 + P378	In case of fire:
P370 + P380	In case of fire: Evacuate area.
P370 + P380 + P375	In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion.
P371 + P380 + P375	In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion.
Storage
Code	Phrase
P401
P402	Store in a dry place.
P403	Store in a well-ventilated place.
P404	Store in a closed container.
P405	Store locked up.
P406	Store in corrosive resistant/ container with a resistant inner liner.
P407	Maintain air gap between stacks/pallets.
P410	Protect from sunlight.
P411
P412	Do not expose to temperatures exceeding 50 oC/ 122 oF.
P413
P420	Store away from other materials.
P422
P402 + P404	Store in a dry place. Store in a closed container.
P403 + P233	Store in a well-ventilated place. Keep container tightly closed.
P403 + P235	Store in a well-ventilated place. Keep cool.
P410 + P403	Protect from sunlight. Store in a well-ventilated place.
P410 + P412	Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF.
P411 + P235	Keep cool.
Disposal
Code	Phrase
P501	Dispose of contents/container to ...
P502	Refer to manufacturer/supplier for information on recovery/recycling

Physical hazards
Code	Phrase
H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
H203	Explosive; fire, blast or projection hazard
H204	Fire or projection hazard
H205	May mass explode in fire
H220	Extremely flammable gas
H221	Flammable gas
H222	Extremely flammable aerosol
H223	Flammable aerosol
H224	Extremely flammable liquid and vapour
H225	Highly flammable liquid and vapour
H226	Flammable liquid and vapour
H227	Combustible liquid
H228	Flammable solid
H229	Pressurized container: may burst if heated
H230	May react explosively even in the absence of air
H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
H241	Heating may cause a fire or explosion
H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
H251	Self-heating; may catch fire
H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
H270	May cause or intensify fire; oxidizer
H271	May cause fire or explosion; strong oxidizer
H272	May intensify fire; oxidizer
H280	Contains gas under pressure; may explode if heated
H281	Contains refrigerated gas; may cause cryogenic burns or injury
H290	May be corrosive to metals
Health hazards
Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed
H304	May be fatal if swallowed and enters airways
H305	May be harmful if swallowed and enters airways
H310	Fatal in contact with skin
H311	Toxic in contact with skin
H312	Harmful in contact with skin
H313	May be harmful in contact with skin
H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
H317	May cause an allergic skin reaction
H318	Causes serious eye damage
H319	Causes serious eye irritation
H320	Causes eye irritation
H330	Fatal if inhaled
H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
H335	May cause respiratory irritation
H336	May cause drowsiness or dizziness
H340	May cause genetic defects
H341	Suspected of causing genetic defects
H350	May cause cancer
H351	Suspected of causing cancer
H360	May damage fertility or the unborn child
H361	Suspected of damaging fertility or the unborn child
H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

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CAS No.: 105580-41-4

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