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[ CAS No. 119141-88-7 ] {[proInfo.proName]}

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Chemical Structure| 119141-88-7
Chemical Structure| 119141-88-7
Structure of 119141-88-7 * Storage: {[proInfo.prStorage]}
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Product Details of [ 119141-88-7 ]

CAS No. :119141-88-7 MDL No. :MFCD09907604
Formula : C17H19N3O3S Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W : 345.42 Pubchem ID :-
Synonyms :
(S)-Omeprazole;(-)-Omeprazole;(–)-Omeprazole

Calculated chemistry of [ 119141-88-7 ]

Physicochemical Properties

Num. heavy atoms : 24
Num. arom. heavy atoms : 15
Fraction Csp3 : 0.29
Num. rotatable bonds : 5
Num. H-bond acceptors : 5.0
Num. H-bond donors : 1.0
Molar Refractivity : 93.7
TPSA : 96.31 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : Yes
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : Yes
CYP2C9 inhibitor : No
CYP2D6 inhibitor : Yes
CYP3A4 inhibitor : Yes
Log Kp (skin permeation) : -6.82 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.64
Log Po/w (XLOGP3) : 2.23
Log Po/w (WLOGP) : 3.61
Log Po/w (MLOGP) : 0.91
Log Po/w (SILICOS-IT) : 3.16
Consensus Log Po/w : 2.31

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.52
Solubility : 0.105 mg/ml ; 0.000303 mol/l
Class : Soluble
Log S (Ali) : -3.89
Solubility : 0.0447 mg/ml ; 0.000129 mol/l
Class : Soluble
Log S (SILICOS-IT) : -6.47
Solubility : 0.000117 mg/ml ; 0.000000337 mol/l
Class : Poorly soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 0.0
Synthetic accessibility : 3.58

Safety of [ 119141-88-7 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P264-P270-P280-P301+P310+P330-P305+P351+P338+P310-P405-P501 UN#:N/A
Hazard Statements:H302-H315-H319 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 119141-88-7 ]

* 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 [ 119141-88-7 ]
  • Downstream synthetic route of [ 119141-88-7 ]

[ 119141-88-7 ] Synthesis Path-Upstream   1~3

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YieldReaction ConditionsOperation in experiment
49 % ee With dihydrogen peroxide In water; acetonitrile at 20℃; for 5.5 h; 5-Methoxy-2-[[(4-methoxy-3,5-dimethyl-2-pyridyl)methyl]thio]-1 H- benzimidazole (4a) and the (salen)manganese complex 2a - e are dissolved in acetonitrile. The reaction temperature is adjusted, then 30percent aqueous H2O2 is added dropwise and the mixture is stirred for several hours. Then the reaction mixture is transferred portion-wise into a cold (0 0C) 10percent aqueous solution of Na2SO3 and stirred for additional 15 min. The obtained mixture is extracted with dichloromethane. The organic phase is dried over Na2SO4 and concentrated yielding an oily residue which is analyzed by chiral and achiral HPLC analytical method.Typically, runs were carried out on 0.5 - 6 mmol scale of the starting material 4a in acetonitrile (1 mmol 4a in 10 mL MeCN). The amounts of added reagents, temperature and reaction time in particular examples are indicated in Tables 1 to 3. Also the results are indicated in Tables 1-3.
80 % ee
Stage #1: at 50 - 55℃; for 1 h;
Stage #2: With N-ethyl-N,N-diisopropylamine In toluene at 25 - 30℃; for 0.0833333 h;
Stage #3: With Cumene hydroperoxide In toluene at 20℃; for 4 h;
0.495 g (1.5 mmol) of the compound of formula III, 5 ml of dried toluene and 1 mmol of a chiral ligand (166.1 mg of the methyl ester of (S)-mandelic acid (general formula IV: X = OMe, Y = H, rVc)) were placed in a 3 -neck 50-ml flask, which was equipped with a magnetic stirrer and a thermometer. The mixture in the flask was heated in an oil bath to a temperature in the range of 50 to 55 °C. Then, 0.15 ml of Ti(Oz-Pr)4 (general formula V: Z = Ti, R5 = i-Pr) were added to this mixture at once. The resulting mixture was stirred at a temperature in the range of 50 to 55 °C for 1 hour. Then, the temperature of the reaction mixture was maintained at 25 to 30 °C and 85 μ of diisopropylethylamine were added to the reaction mixture. The mixture was stirred for 5 minutes and 0.25 ml of 88percent cumene hydroperoxide were added to the solution. The resulting reaction mixture was stirred at the room temperature for 4 hours. The reaction was terminated by addition of 5 ml of a 5percent aqueous solution of Na2S203 and diluted with 5 ml of toluene. The resulting mixture was filtered through filtration paper. The two-phase filtrate was divided in a separating funnel and the toluene fraction was extracted with additional 5 ml of water. After drying with anhydrous magnesium sulfate the toluene solution was evaporated to dryness in a rotational vacuum evaporator. The resulting evaporation residue was chromatographed on silica gel. Chloroform : methanol : 25percent NH OH in the (10 : 1 : 0.1) proportion was used as the eluent. The fractions of the product were combined, evaporated in a rotational vacuum evaporator and analyzed in a HPLC system on a chiral phase (CHIRALPAK AD-H.(R).); mobile phase 50percent of hexane : 50percent of ethanol, detection 302 nm).Esomeprazole (formula I) with the enantiomeric excess of 80 percent was obtained.
67.7 % ee
Stage #1: at 50 - 55℃; for 1 h;
Stage #2: With N-ethyl-N,N-diisopropylamine In toluene at 25 - 30℃; for 0.0833333 h;
Stage #3: With Cumene hydroperoxide In toluene at 20℃; for 4 h;
(R)-omeprazole was prepared with the same procedure as described in example 1. 1 mmol (200 mg) of (jf?)-3-chloromandelic acid methyl ester (general formula ent-TV: X = OMe, Y = 3-Cl) was used as the chiral ligand.(/?)-omeprazole (formula ent-I) with the enantiomeric excess of 67.6 percent was obtained.
83.7 % ee With oxygen; NADP In aq. phosphate buffer; isopropyl alcohol at 25℃; for 24 h; Enzymatic reaction General procedure: The Activity FIOP and enantioselectivity (percent ee) of the 53 exemplary non-naturally occurring monooxygenase polypeptides of Table 2B in carrying out the biocatalytic conversion of the substrate compound (1) (pyrmetazole) to the product compound (2) ((R)- or (S)-omeprazole) were determined that following general HTP assay conditions: 5 g/L pyrmetazole substrate, 10 μL of lysate of the engineered CHMO polypeptide, 1 g/L KRED of SEQ ID NO: 268, 0.5 g/L NADP, in a solution of 50 mM potassium phosphate buffer, 10percent (v/v) IPA, pH 9.0, 25° C. reaction temperature and 24 h reaction time (with 400 rpm stirring). Further details of the HTP assay methods are described in the Examples.
82.5 % ee With C64H64N4O6Ti2; dihydrogen peroxide In water; ethyl acetate at 0℃; for 24 h; General procedure: Sulfide (OMS or LPS, 100 mol) and the Ti-salalen catalyst(1.1 mol) were dissolved in the solvent (typically: EtOAc, 6.0 mL),the mixture was thermostatted at desired temperature (typically 0 °C, or −20 to +20 °C for variable-temperature measurements),and 30percent aqueous hydrogen peroxide (0.105 mmol of H2O2) was then introduced in one portion. Stirring (500 rpm) was continued at that temperature (typically 24 h). For low-temperature experiments, the reaction times were about 30 h at −10 °C and up to 10 days at −20 °C. To analyze the reaction outcome, 20 L aliquots of the reaction mixture were taken to a vial and immediately carefully evaporated to dryness with a stream of compressed air during ca. 15–20 s. The remaining solid was dissolved in 0.20 mL of 1percent Et3N solution in isopropyl alcohol, and the contents of residual sulfide, (R)- and(S)-sulfoxide, and sulfone, were analyzed by chiral HPLC as noted above.
71.5 % ee With C68H72N4O10Ti2; dihydrogen peroxide In water; ethyl acetate at 0℃; for 24 h; General procedure: Sulfide (OMS or LPS, 100 mol) and the Ti-salalen catalyst(1.1 mol) were dissolved in the solvent (typically: EtOAc, 6.0 mL),the mixture was thermostatted at desired temperature (typically 0 °C, or −20 to +20 °C for variable-temperature measurements),and 30percent aqueous hydrogen peroxide (0.105 mmol of H2O2) was then introduced in one portion. Stirring (500 rpm) was continued at that temperature (typically 24 h). For low-temperature experiments, the reaction times were about 30 h at −10 °C and up to 10 days at −20 °C. To analyze the reaction outcome, 20 L aliquots of the reaction mixture were taken to a vial and immediately carefully evaporated to dryness with a stream of compressed air during ca. 15–20 s. The remaining solid was dissolved in 0.20 mL of 1percent Et3N solution in isopropyl alcohol, and the contents of residual sulfide, (R)- and(S)-sulfoxide, and sulfone, were analyzed by chiral HPLC as noted above.
68 % ee With dihydrogen peroxide; acetic acid In methanol; water at 0℃; for 12 h; General procedure: The appropriate catalyst 5 (10 molpercent) and sulfide (1.0 mmol) were dissolved in CH3OH/H2O (1:1) (5 mL) and this solution was cooled to 0 °C. Subsequently the additive HOAc (2.0 mmol) and the oxidant hydrogen peroxide (1.5 mmol, 30percent, w/w) were added. The mixture was stirred for 12 h and then was treated with 10 mL of saturated ammonium chloridesolution and extracted with ethyl acetate. The organic layer was dried (MgSO4), filtered and concentrated to give pure sulfoxides through flash column chromatography on silica gel (hexane/ethyl acetate(10:1)). All the products in the paper are known compounds that exhibited spectroscopic data identical to those reported in the literature [34]. The ee was determined by HPLC on chiral column (Daicel,Chiralpak, OD-H). The configuration of sulfoxides product from these reactions was proven to be (S) by comparing the specific rotation with the literature values [35].

Reference: [1] Patent: WO2007/88559, 2007, A1, . Location in patent: Page/Page column 9-10
[2] Patent: WO2007/88559, 2007, A1, . Location in patent: Page/Page column 10
[3] Russian Journal of Organic Chemistry, 2008, vol. 44, # 1, p. 124 - 127
[4] Synthesis, 2008, # 16, p. 2513 - 2518
[5] European Journal of Organic Chemistry, 2009, # 7, p. 987 - 991
[6] Patent: WO2010/43601, 2010, A1, . Location in patent: Page/Page column 23; 25
[7] Patent: WO2010/91652, 2010, A1, . Location in patent: Page/Page column 14
[8] Patent: WO2011/120475, 2011, A1, . Location in patent: Page/Page column 13; 14
[9] Patent: WO2011/120475, 2011, A1, . Location in patent: Page/Page column 14
[10] Tetrahedron Asymmetry, 2012, vol. 23, # 6-7, p. 457 - 460
[11] RSC Advances, 2014, vol. 4, # 87, p. 46545 - 46554
[12] Patent: US9228216, 2016, B2, . Location in patent: Page/Page column 50-52
[13] Catalysis Today, 2017, vol. 279, p. 84 - 89
[14] Catalysis Today, 2017, vol. 279, p. 84 - 89
[15] Catalysis Communications, 2017, vol. 92, p. 114 - 118
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YieldReaction ConditionsOperation in experiment
67 % ee With dihydrogen peroxide In water; acetonitrile at -10℃; for 5 h; 5-Methoxy-2-[[(4-methoxy-3,5-dimethyl-2-pyridyl)methyl]thio]-1 H-benzimidazole (4a) (0.987 g , 3 mmol) and manganese complex of (R,R)-1 ,2-bis(3,5-di-te/f-butyl-2-hydoxybenzyl- amino)cyclohexane (10c) (96 mg, 5 mol percent) are dissolved in acetonitrile (45 ml). The reaction mixture is cooled to -100C and 30percent aqueous H2O2 (13.8 ml, 45 mol equiv) is added dropwise over 3 hours period. The reaction mixture is stirred for additional 2 hours. HPLC analysis shows formation of 56percent of sulfoxide (1a) with 67percent ee (S-enriched) and 5percent of sulfone.
9 % ee With dihydrogen peroxide In water; acetonitrile at 0 - 20℃; for 3.5 h; 5-Methoxy-2-[[(4-methoxy-3,5-dimethyl-2-pyridyl)methyl]thio]-1 H- benzimidazole (4a) and a preformed salan (10b) - metal complex are dissolved in acetonitrile. The reaction temperature is adjusted and 30percent aqueous H2O2 is added dropwise. The mixture is stirred for several hours. Then, it is poured portionwise into a cold (0 0C) 10percent aqueous Na2SO3 and stirred for additional 15 min and extracted with dichloromethane. The organic phase is dried over Na2SO4 and concentrated yielding an oily residue which is analyzed by chiral and achiral HPLC.Typically, runs were carried out on 1 mmol scale of the starting material 4a in acetonitrile (1 mmol 4a in 10 mL MeCN). The amounts of added reagents, temperature and reaction time in particular examples are indicated in Table 4. Also the results are indicated in Table 4.
75.1 % ee
Stage #1: With titanium(IV) isopropylate; C69H72N6O3 In water; toluene at 50℃; for 1 h; Inert atmosphere
Stage #2: With p-cumenyl hydroperoxide; N-ethyl-N,N-diisopropylamine In water; toluene at 25℃; for 0.5 h;
Titanium tetraisopropoxide (66.7 mg, 0.235 mmol) and water (8.0 mg, the total amount of water is 8.47 mg, 0.47 mmol) were added to a solution of L1 (67.1 mg, 0.065 mmol) in toluene (20 mL) at 25 C. After stirring at that temperature for 1 h, pyrmetazol (165.0 mg, 0.5 mmol) was added. Then, the mixture was heated to 50 Cand maintained for 1 h. After the mixture was cooled to 25 C, N,N-diisopropylethylamine (16.8 mg, 0.13 mol) and cumene hydroperoxide (80percent in cumene, 110.5 mg,0.65 mmol) were added subsequently. After stirring at 25 C for 1 h, a small sample of reaction mixture was taken for HPLC analysis for conversion and selectivity, and the product was isolated by preparative thin-layer chromatography (TLC; eluent: CH2Cl2/MeOH 25/1) for determination of the enantiomeric purity.
Reference: [1] Patent: WO2009/66321, 2009, A2, . Location in patent: Page/Page column 19
[2] Patent: WO2009/66321, 2009, A2, . Location in patent: Page/Page column 19-20
[3] Patent: WO2010/43601, 2010, A1, . Location in patent: Page/Page column 31
[4] Patent: WO2010/43601, 2010, A1, . Location in patent: Page/Page column 30; 31
[5] Synthetic Communications, 2015, vol. 45, # 1, p. 70 - 77
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Reference: [1] Patent: US2005/267157, 2005, A1, . Location in patent: Page/Page column 10-11
[2] Patent: US2005/267157, 2005, A1, . Location in patent: Page/Page column 11
[3] Patent: US2005/267157, 2005, A1, . Location in patent: Page/Page column 11
[4] Patent: US2007/149573, 2007, A1, . Location in patent: Page/Page column 5
[5] Patent: EP2143722, 2010, A1, . Location in patent: Page/Page column 9
[6] Patent: EP1947099, 2008, A1, . Location in patent: Page/Page column 11-12
[7] Organic Letters, 2013, vol. 15, # 22, p. 5658 - 5661
[8] Chemical Communications, 2017, vol. 53, # 3, p. 509 - 512
[9] Journal of Organic Chemistry, 2018, vol. 83, # 14, p. 7453 - 7458
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