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[ CAS No. 29833-32-7 ] {[proInfo.proName]}

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Chemical Structure| 29833-32-7
Chemical Structure| 29833-32-7
Structure of 29833-32-7 * Storage: {[proInfo.prStorage]}
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Product Details of [ 29833-32-7 ]

CAS No. :29833-32-7 MDL No. :MFCD03161190
Formula : C12H26ClNO2 Boiling Point : -
Linear Structure Formula :- InChI Key :IWHIKEQZPPYMOH-UHFFFAOYSA-N
M.W : 251.79 Pubchem ID :12720706
Synonyms :

Calculated chemistry of [ 29833-32-7 ]

Physicochemical Properties

Num. heavy atoms : 16
Num. arom. heavy atoms : 0
Fraction Csp3 : 0.92
Num. rotatable bonds : 11
Num. H-bond acceptors : 3.0
Num. H-bond donors : 1.0
Molar Refractivity : 70.76
TPSA : 52.32 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : Yes
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -4.74 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.0
Log Po/w (XLOGP3) : 4.36
Log Po/w (WLOGP) : 3.43
Log Po/w (MLOGP) : 2.54
Log Po/w (SILICOS-IT) : 2.86
Consensus Log Po/w : 2.64

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 1.0
Egan : 0.0
Muegge : 0.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -3.42
Solubility : 0.0953 mg/ml ; 0.000379 mol/l
Class : Soluble
Log S (Ali) : -5.17
Solubility : 0.00169 mg/ml ; 0.00000669 mol/l
Class : Moderately soluble
Log S (SILICOS-IT) : -3.65
Solubility : 0.056 mg/ml ; 0.000222 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 2.0
Synthetic accessibility : 2.03

Safety of [ 29833-32-7 ]

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

Application In Synthesis of [ 29833-32-7 ]

* 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.

  • Downstream synthetic route of [ 29833-32-7 ]

[ 29833-32-7 ] Synthesis Path-Downstream   1~85

  • 1
  • [ 3422-91-1 ]
  • [ 29833-32-7 ]
  • [ 103714-08-5 ]
  • 2
  • [ 590-28-3 ]
  • [ 29833-32-7 ]
  • [ 17994-85-3 ]
  • 3
  • [ 29833-32-7 ]
  • [ 501-53-1 ]
  • [ 98603-11-3 ]
  • 4
  • [ 29833-32-7 ]
  • lupa-2(3),20(29)-dien-28-oyl chloride [ No CAS ]
  • [ 173106-20-2 ]
  • 5
  • [ 29833-32-7 ]
  • [ 173106-56-4 ]
  • [ 173106-10-0 ]
  • 7
  • [ 29833-32-7 ]
  • [ 173106-51-9 ]
  • [ 173106-52-0 ]
  • 8
  • [ 29833-32-7 ]
  • (1R,3aS,5aR,5bR,7aR,11aR,11bR,13aR,13bR)-10-Hydroxy-1-isopropenyl-5a,5b,8,8,11a-pentamethyl-9-oxo-1,2,3,4,5,5a,5b,6,7,7a,8,9,11a,11b,12,13,13a,13b-octadecahydro-cyclopenta[a]chrysene-3a-carbonyl chloride [ No CAS ]
  • [ 173106-23-5 ]
  • 9
  • [ 29833-32-7 ]
  • [ 150841-20-6 ]
  • [ 150841-19-3 ]
  • 10
  • [ 29833-32-7 ]
  • [ 150840-98-5 ]
  • 11-[((1R,3aS,5aR,5bR,7aR,9R,11aR,11bR,13aR,13bR)-9-Acetoxy-1-isopropenyl-5a,5b,8,8,11a-pentamethyl-icosahydro-cyclopenta[a]chrysene-3a-carbonyl)-amino]-undecanoic acid methyl ester [ No CAS ]
  • 11
  • [ 29833-32-7 ]
  • [ 59868-82-5 ]
  • [ 150840-96-3 ]
  • 12
  • [ 29833-32-7 ]
  • vancomycin [ No CAS ]
  • C78H98Cl2N10O25 [ No CAS ]
  • 13
  • N-Boc-(S/R)-valine [ No CAS ]
  • [ 29833-32-7 ]
  • [ 805231-75-8 ]
  • 14
  • [ 13139-15-6 ]
  • [ 29833-32-7 ]
  • [ 805230-89-1 ]
  • 15
  • [ 4530-18-1 ]
  • [ 29833-32-7 ]
  • [ 805230-93-7 ]
  • 16
  • [ 13734-41-3 ]
  • [ 29833-32-7 ]
  • [ 805230-90-4 ]
  • 17
  • [ 13139-15-6 ]
  • [ 29833-32-7 ]
  • [ 805230-88-0 ]
  • 18
  • [ 13734-34-4 ]
  • [ 29833-32-7 ]
  • [ 805230-92-6 ]
  • 19
  • [ 33125-05-2 ]
  • [ 29833-32-7 ]
  • [ 805230-91-5 ]
  • 20
  • [ 29833-32-7 ]
  • 2-(tert-butoxycarbonylamino)-2-phenylacetic acid [ No CAS ]
  • [ 805231-14-5 ]
  • 21
  • [ 29833-32-7 ]
  • [ 384330-49-8 ]
  • 1,2-bis{5'-[10''-(methoxycarbonyl)-decylcarbamoyl]-2'-methylthien-3'-yl}perfluorocyclopentene [ No CAS ]
  • 22
  • [ 29833-32-7 ]
  • [ 805230-96-0 ]
  • 23
  • [ 29833-32-7 ]
  • [ 805230-94-8 ]
  • 24
  • [ 29833-32-7 ]
  • [ 805230-99-3 ]
  • 25
  • [ 29833-32-7 ]
  • [ 805230-98-2 ]
  • 26
  • [ 29833-32-7 ]
  • [ 805231-01-0 ]
  • 27
  • [ 29833-32-7 ]
  • [ 805231-00-9 ]
  • 28
  • [ 29833-32-7 ]
  • [ 805231-03-2 ]
  • 29
  • [ 29833-32-7 ]
  • [ 676248-49-0 ]
  • 30
  • [ 29833-32-7 ]
  • [ 805231-02-1 ]
  • 31
  • [ 29833-32-7 ]
  • [ 805231-17-8 ]
  • 32
  • [ 29833-32-7 ]
  • [ 805231-04-3 ]
  • 33
  • [ 29833-32-7 ]
  • [ 676248-54-7 ]
  • 34
  • [ 29833-32-7 ]
  • [ 805231-07-6 ]
  • 35
  • [ 29833-32-7 ]
  • [ 676248-53-6 ]
  • 36
  • [ 29833-32-7 ]
  • [ 805231-06-5 ]
  • 37
  • [ 29833-32-7 ]
  • [ 805231-10-1 ]
  • 38
  • [ 29833-32-7 ]
  • [ 805231-05-4 ]
  • 39
  • [ 29833-32-7 ]
  • [ 805231-09-8 ]
  • 40
  • [ 29833-32-7 ]
  • sodium 11-[(2R,S)-2-(dodecanoylamino)-2-phenylethanoyl]amino}undecanoate [ No CAS ]
  • 41
  • [ 29833-32-7 ]
  • sodium 11-[(2R,S2)-2-(dodecanoylamino)-3-phenylpropanoyl]amino}undecanoate [ No CAS ]
  • 42
  • [ 29833-32-7 ]
  • sodium 11-[(2R)-2-(dodecanoylamino)-2-phenylethanoyl]amino}undecanoate [ No CAS ]
  • 43
  • [ 29833-32-7 ]
  • 11-[((1R,3aS,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-9-Hydroxy-1-isopropenyl-5a,5b,8,8,11a-pentamethyl-icosahydro-cyclopenta[a]chrysen-3a-ylmethyl)-amino]-undecanoic acid [ No CAS ]
  • 44
  • [ 29833-32-7 ]
  • [ 173106-53-1 ]
  • 45
  • [ 29833-32-7 ]
  • 11-[((1R,3aS,5aR,5bR,7aS,11aS,11bR,13aR,13bR)-1-Isopropenyl-5a,5b,8,8,11a-pentamethyl-1,2,3,4,5,5a,5b,6,7,7a,8,11,11a,11b,12,13,13a,13b-octadecahydro-cyclopenta[a]chrysene-3a-carbonyl)-amino]-undecanoic acid [ No CAS ]
  • 46
  • [ 29833-32-7 ]
  • 11-[((1R,3aS,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-1-Isopropenyl-9-methoxy-5a,5b,8,8,11a-pentamethyl-icosahydro-cyclopenta[a]chrysene-3a-carbonyl)-amino]-undecanoic acid [ No CAS ]
  • 47
  • [ 29833-32-7 ]
  • [ 24255-66-1 ]
  • 48
  • [ 29833-32-7 ]
  • [ 98603-12-4 ]
  • 49
  • [ 29833-32-7 ]
  • [ 98603-14-6 ]
  • 50
  • [ 29833-32-7 ]
  • benzene-1,3,5-tris(11-carboxyundecyl-N-methylcarboxamide) trisodium salt [ No CAS ]
  • 52
  • [ 29833-32-7 ]
  • Bis-ω-amimo-undecansaeure-hydrazid [ No CAS ]
  • 53
  • [ 29833-32-7 ]
  • [ 101121-13-5 ]
  • 54
  • 3β-acetoxy-20(29)-lupen-28-oyl chloride [ No CAS ]
  • [ 29833-32-7 ]
  • methyl N-[3β-acetoxy-20(29)-lupen-28-oyl]-11-aminoundecanoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
With triethylamine; In dichloromethane; EXAMPLE 6 580 mg of <strong>[29833-32-7]methyl 11-aminoundecanoate hydrochloride</strong> and then 0.62 cm3 of triethylamine are added to a solution of 1.03 g of 3β-acetoxy-20(29)-lupen-28-oyl chloride in 30 cm3 of dichloromethane. The solution is then stirred for 48 hours at a temperature in the region of 20 C. and the solvent is evaporated to dryness under reduced pressure (2.7 kPa) at a temperature in the region of 20 C. 2 g of a yellow foam are obtained which are chromatographed on a column with a diameter of 2.7 cm containing 80 g of silica (0.02-0.045 mm) eluted with diisopropyl ether while collecting 20 cm3 fractions. After discarding the first 10 fractions, the 6 following are combined and concentrated under reduced pressure (2.7 kPa) at a temperature in the region of 30 C. 1.29 g of methyl N-[3β-acetoxy-20(29)-lupen- 28-oyl]-11-aminoundecanoate is thus obtained in the form of a white foam.
  • 55
  • 3α-acetoxy-20(29)-lupen-28-oyl chloride [ No CAS ]
  • [ 29833-32-7 ]
  • methyl N-[3α-acetoxy-20(29)-lupen-28-oyl]-11-aminoundecanoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
With triethylamine; In diethyl ether; cyclohexane; ethyl acetate; EXAMPLE 7 243 mg of <strong>[29833-32-7]methyl 11-aminoundecanoate hydrochloride</strong> and then 0.27 cm3 of triethylamine are added to 20 cm3 of a 50/50 (by volume) tetrahydrofuran/chloroform mixture containing 453 mg of 3α-acetoxy-20(29)-lupen-28-oyl chloride. The solution is stirred for 20 hours at a temperature in the region of 20 C. and the solvent is evaporated to dryness under reduced pressure (2.7 kPa) at a temperature in the region of 30 C. The residue is taken up in 60 cm3 of ethyl ether and 25 cm3 of distilled water, the organic phase is separated off and the aqueous phase is extracted with a total of 25 cm3 of ethyl ether. The combined organic phases are washed with a total of 45 cm3 of distilled water, dried over anhydrous magnesium sulphate and concentrated to dryness under reduced pressure (2.7 kPa) at a temperature in the region of 30 C. The 600 mg of light yellow foam obtained are chromatographed on a column with a diameter of 2.5 cm containing 56 g of silica (0.063-0.200 mm) eluted with a 85/15 (by volume) mixture of cyclohexane and ethyl acetate while collecting 7 cm3 fractions. The first 10 fractions are discarded; the following 17 are combined and concentrated under reduced pressure (2.7 kPa) at a temperature in the region of 30 C. 810 mg of methyl N-[3α-acetoxy-20(29)-lupen-28-oyl]-11-aminoundecanoate are thus obtained in the form of a white foam.
  • 56
  • 3-oxo-20(29)-lupen-28-oyl chloride [ No CAS ]
  • 3-oxo-20(29)-lupen-28-oic acid [ No CAS ]
  • [ 29833-32-7 ]
  • methyl N-[3-oxo-20(29)-lupen-28-oyl]-11-aminoundecanoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
With triethylamine; In methanol; dichloromethane; chloroform; EXAMPLE 8 610 mg of <strong>[29833-32-7]methyl 11-aminoundecanoate hydrochloride</strong> and then 0.68 cm3 of triethylamine are added to 20 cm3 of a chloroform solution of 3-oxo-20(29)-lupen-28-oyl chloride (prepared from 1 g of 3-oxo-20(29)-lupen-28-oic acid). The solution is then stirred for 15 hours at a temperature in the region of 20 C. After addition of 40 cm3 of distilled water, the organic phase is separated off and the aqueous phase is extracted with a total of 30 cm3 of chloroform. The combined organic phases are washed with a total of 30 cm3 of distilled water, dried over anhydrous sodium sulphate and concentrated to dryness under reduced pressure (2.7 kPa) at a temperature in the region of 40 C. 1.5 g of a yellow foam is obtained which is chromatographed on a column with a diameter of 3.5 cm containing 150 g of silica (0.02- 0.045 mm) eluted with a 98/2 (by volume) mixture of methylene chloride and methanol while collecting 20 cm3 fractions. After discarding the first 45 fractions, the following 30 are combined and concentrated under reduced pressure (2.7 kPa) at a temperature in the region of 50 C. 1.1 g of methyl N-[3-oxo-20(29)-lupen-28-oyl]-11-aminoundecanoate is thus obtained in the form of a white foam. [Rf =0.5; silica thin layer chromatography; eluent: dichloromethane/ethanol 98/2 (by volume)].
  • 57
  • 30-acetoxy-3-oxo-20(29)-lupen-28-oyl chloride [ No CAS ]
  • [ 29833-32-7 ]
  • methyl N-[30-acetoxy-3-oxo-20(29)-lupen-28-oyl]-11-aminoundecanoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
With triethylamine; In dichloromethane; cyclohexane; ethyl acetate; EXAMPLE 9 380 mg of <strong>[29833-32-7]methyl 11-aminoundecanoate hydrochloride</strong> and then 0.56 cm3 of triethylamine are added to a solution of 800 mg of 30-acetoxy-3-oxo-20(29)-lupen-28-oyl chloride in 40 cm3 of dichloromethane. The solution is then stirred for 1 hour and 30 minutes at a temperature in the region of 20 C. and the solvent is evaporated to dryness under reduced pressure (2.7 kPa) at a temperature in the region of 35 C. The residue obtained is chromatographed on a column with a diameter of 4 cm containing 125 g of silica (0.02-0.045 mm) eluted with a 6/4 (by volume) mixture of cyclohexane and ethyl acetate while collecting 25 cm3 fractions. The first 9 fractions obtained are discarded, the following 6 are concentrated to dryness under reduced pressure (2.7 kPa) at a temperature in the region of 45 C. 960 mg of methyl N-[30-acetoxy-3-oxo-20(29)-lupen-28-oyl]-11-aminoundecanoate are thus obtained in the form of a colourless lac.
  • 58
  • 3β,30-diacetoxy-20(29)-lupen-28-oic acid [ No CAS ]
  • [ 29833-32-7 ]
  • methyl N-[3β,30-diacetoxy-20(29)-lupen-28-oyl]-11-aminoundecanoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
With triethylamine; In dichloromethane; cyclohexane; water; ethyl acetate; EXAMPLE 11 280 mg of <strong>[29833-32-7]methyl 11-aminoundecanoate hydrochloride</strong> and 0.28 cm3 of triethylamine are added to 25 cm3 of a solution, in dichloromethane, of 3β,30-diacetoxy-20(29)-lupen-28-oyl chloride (prepared from 560 mg of 3β,30-diacetoxy-20(29)-lupen-28-oic acid). The solution is then stirred for 12 hours at a temperature in the region of 20 C. 10 cm3 of distilled water are then added. The organic phase is separated off and then washed with a total of 20 cm3 of distilled water. The combined organic phases are dried over anhydrous magnesium sulphate and concentrated to dryness under reduced pressure (2.7 kPa) at a temperature in the region of 35 C. The colourless oil obtained (750 mg) is chromatographed on a column with a diameter of 1.7 cm containing 15 g of silica (0.02-0,045 mm) eluted with an 80/20 (by volume) mixture of cyclohexane and ethyl acetate while collecting 15 cm3 fractions. The first 2 fractions obtained are discarded, the following 5 are concentrated to dryness under reduced pressure (22 kPa) at a temperature in the region of 40 C. 650 mg of methyl N-[3β,30-diacetoxy-20(29)-lupen-28-oyl]-11-aminoundecanoate are thus obtained in the form of a white lac [Rf =0.28; silica thin layer chromatography; eluent: cyclohexane/ethyl acetate] 80/20 (by volume).
  • 59
  • 30-nor-3β-acetoxy-20-oxo-28-lupanoyl chloride [ No CAS ]
  • [ 29833-32-7 ]
  • methyl N-(30-nor-3β-acetoxy-20-oxo-28-lupanoyl)-11-aminoundecanoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
With triethylamine; In dichloromethane; di-isopropyl ether; cyclohexane; ethyl acetate; EXAMPLE 15 2.2 cm3 of triethylamine and 1.94 g of <strong>[29833-32-7]methyl 11-aminoundecanoate hydrochloride</strong> are added to 195 cm3 of a methylene chloride solution of 30-nor-3β-acetoxy-20-oxo-28-lupanoyl chloride. The solution is then stirred for 72 hours at a temperature in the region of 20 C. The reaction mixture is diluted with 100 cm3 of dichloromethane and the organic phase is washed with 3 times 150 cm3 of distilled water. The combined organic phases are dried for 3 hours over magnesium sulphate and filtered. The organic phases are concentrated to dryness under reduced pressure (2.7 kPa) at a temperature in the region of 50 C. The pale yellow oil obtained (5.7 g) is chromatographed on a column with a diameter of 4 cm and a height of 60 cm containing silica (0.02-0.045 nun) and eluted successively with a 70/30 (by volume) mixture of cyclohexane and ethyl acetate for the fractions 1 to 50 and a 50/50 (by volume) mixture of cyclohexane and ethyl acetate for the following fractions. 100 cm3 fractions are collected. The first 30 fractions are discarded; the following 32 are combined and concentrated under reduced pressure (2.7 kPa) at a temperature in the region of 35 C. 5 g are thus obtained of a white foam which is triturated with 2 times 100 cm3 of diisopropyl ether and then dried under reduced pressure (2.7 kPa) at a temperature in the region of 40 C. 4.75 g of methyl N-(30-nor-3β-acetoxy-20-oxo-28-lupanoyl)-11-aminoundecanoate are thus obtained in the form of a white foam [Rf =0.23; silica thin layer chromatography; eluent cyclohexane/ethyl acetate 8/2 (by volume)].
  • 60
  • [ 79-37-8 ]
  • [ 29833-32-7 ]
  • [ 91702-98-6 ]
  • (+/-)-11-[[2-[(acetylthio)methyl]-1-oxo-3-phenylpropyl]amino]undecanoic acid, methyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
With N-ethyl-N,N-diisopropylamine;N-methyl-acetamide; In tetrahydrofuran; diethyl ether; dichloromethane; ethyl acetate; (b) (+-)-11-[[2-[(Acetylthio)methyl]-1-oxo-3-phenylpropyl]amino]undecanoic acid, methyl ester Oxalyl chloride (0.54 ml., 6.2 mmole) is added to a solution of <strong>[91702-98-6]3-acetylthio-2-benzylpropanoic acid</strong> (1.43 g., 6 mmole) in ethyl ether (10 ml.). This mixture is cautiously treated with a catalytic amount (3 drops) of dimethylformamide, and then stirred for one hour at room temperature. The mixture is concentrated in vacuo producing an oil which is dissolved in tetrahydrofuran (10 ml.) and again concentrated in vacuo. The resulting residue is dissolved in methylene chloride (6 ml.) and added dropwise over ten minutes to a cold (-5), stirred solution of 11-aminoundecanoic acid, methyl ester, hydrochloride (1:1) (1.61 g., 6.4 mmole) and diisopropylethylamine (2.23 ml., 12.8 mmole) in methylene chloride (11 ml.). After stirring in the cold (-5) for 2.5 hours, the mixture is allowed to warm to room temperature and left to stir overnight. The mixture is then concentrated in vacuo and the residue is taken up into ethyl acetate (100 ml.) and filtered to remove diisopropylethylamine hydrochloride. The filtrate is washed sequentially with 10% potassium bisulfate, water, 5% sodium bicarbonate, water and 50% brine (3*30 ml. each). The organic layer is dried (Na2 SO4) and concentrated to yield 2.5 g. of (+-)-11-[[2-[(acetylthio)methyl]-1-oxo-3-phenylpropyl]amino]undecanoic acid, methyl ester as a light yellow solid; m.p. 64-66.
  • 61
  • [ 2432-99-7 ]
  • [ 29833-32-7 ]
YieldReaction ConditionsOperation in experiment
With thionyl chloride; In methanol; (a) 11-Aminoundecanoic acid, methyl ester, hydrochloride (1:1) Thionyl chloride (5.84 ml., 80 mmole) is added dropwise with stirring to a cold suspension of 11-aminoundecanoic acid (8.05 g., 40 mmole) in methanol (50 ml.) at a rate so as to maintain the reaction temperature between -5 and -10. After the addition of all of the thionyl chloride, the mixture is allowed to warm to room temperature. A white precipitate forms, which is dissolved by adding an additional 50 ml. of methanol to the mixture. The reaction is stirred at room temperature overnight. The mixture is concentrated in vacuo to give a white solid that is triturated in ether (twice) to yield 7.26 g. of 11-aminoundecanoic acid, methyl ester, hydrochloride (1:1); m.p. 155-158.
  • 62
  • [ 1042109-92-1 ]
  • [ 29833-32-7 ]
  • [ 1042110-14-4 ]
YieldReaction ConditionsOperation in experiment
With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 20℃; 4.48 g (15 mmol) of (2,5,2',4',6'-pentamethylbiphenyl-4-yloxy)acetic acid (Example 1c) and 3.78 g (15 mmol) of <strong>[29833-32-7]methyl 11-aminoundecanoate hydrochloride</strong> (Chem. Ber. 94, 2470-2477 (1961)) are taken up in 125 ml of DMF and, after addition of 6.47 ml (37.8 mmol) of N,N-ethyldiisopropylamine and 6.26 g (16.5 mmol) of HBTU, stirred at RT overnight. The resulting crude product is chromatographed on silica gel (dichloromethane/methanol 19:1). The fractions containing the product are combined and evaporated.Yield: 7 g (94.1% of theory)
  • 63
  • maslinic acid [ No CAS ]
  • [ 29833-32-7 ]
  • [ 1137728-58-5 ]
  • 64
  • [ 29833-32-7 ]
  • 6,6,7,7,8,8,9,9,10,10,11,11,12,12,13,13,13-heptadecafluoro-2-(4,4,5,5,6,6,7,7,8,8,9,9,10,10,11,11,11-heptadecafluoroundecyl)tridecanoic chloride [ No CAS ]
  • methyl 11-[6,6,7,7,8,8,9,9,10,10,11,11,12,12,13,13,13-heptadecafluoro-2-(4,4,5,5,6,6,7,7,8,8,9,9,10,10,11,11,11-heptadecafluoroundecyl)-tridecanoylamino]undecanoate [ No CAS ]
  • 65
  • [ 67-56-1 ]
  • [ 2432-99-7 ]
  • [ 29833-32-7 ]
YieldReaction ConditionsOperation in experiment
99% With thionyl chloride; at 20℃;Reflux; General procedure: To a solution of the amino acid 1a-1e (22.45 mmol, 1 mol equiv) in 20-30 cm3 of dry methanol in a two-neck flask with a reflux condenser 2.3 cm3 thionyl chloride (31.43 mmol,1.4 mol equiv) was added drop-wise over 5-10 min. After the addition was complete, the mixture was heated to reflux for 3 h. The reaction mixture was left to stir over night at room temperature. After the reaction was complete, the solvent was removed by evaporation (RVE). The white or light-yellow solid was washed with n-hexane(2 9 50 cm3), and evaporated with another portion of n-hexane. The product was dried at low pressure.
86% With thionyl chloride; at 0℃; for 5h;Reflux; SOCl2 (0.55 mL, 7.6 mmol) was dropwise added to a stirred solution of <strong>[2432-99-7]11-aminoundecanoic acid</strong> (500 mg, 2.49 mmol) solubilized in dry MeOH (5 mL) kept at 0 C. The reaction mixture was refluxed for 5 h. When the reaction was completed, the SOCl2 excess and MeOH were distilled under reduced pressure, using a NaOH trap. The product was isolated as a white solid (535 g, 86% yield). NMR (300 MHz, CDCl3, delta) : 3.64 (s, 3H, OC) ; 2.8-2.5 (m, 2H, NH2C) ; 2.5-2.2 (m, 2H, CCO) ; 2.19 (bs, 3H, NH3 : exchange with D20) , 1.61-1.56 (m, 2H, CCH2CO) ; 1.42-1.41 (m, 2H, CJJ2CH2NH2 ) ; 1.36-1.18 (m, 12H, C).
With thionyl chloride; at -10℃; for 3h;Reflux; General procedure: To a stirred solution 5-aminopentanoic acid (500 mg,4.27 mmol) in anhydrous MeOH (5 mL) kept at -10 C, SOCl2(1.1 mL, d 1.631 g/mL, 15 mmol) was dropwise added. The obtainedreaction mixture was refluxed for 3 h. Then, excess SOCl2and MeOH were distilled under reduced pressure, using a NaOHtrap. The product was obtained as a white solid in 79% yield(645 mg) and used in the following reaction without any furtherpurification.
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  • (5S)-3-(1-hydroxy-11-(3-azido-5-(azidomethyl)-benzamido)undecan-1-ylidene)-5-((R)-1-hydroxyethyl)-1-methylpyrrolidine-2,4-dione [ No CAS ]
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  • [ 1448632-34-5 ]
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