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[ CAS No. 201003-48-7 ] {[proInfo.proName]}

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Cat. No.: {[proInfo.prAm]}
Chemical Structure| 201003-48-7
Chemical Structure| 201003-48-7
Structure of 201003-48-7 * Storage: {[proInfo.prStorage]}
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Quality Control of [ 201003-48-7 ]

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Product Details of [ 201003-48-7 ]

CAS No. :201003-48-7 MDL No. :MFCD00080276
Formula : C29H38N2O6 Boiling Point : -
Linear Structure Formula :- InChI Key :LUGFCMICCJNLBC-VWLOTQADSA-N
M.W : 510.62 Pubchem ID :51340513
Synonyms :

Calculated chemistry of [ 201003-48-7 ]

Physicochemical Properties

Num. heavy atoms : 37
Num. arom. heavy atoms : 12
Fraction Csp3 : 0.48
Num. rotatable bonds : 15
Num. H-bond acceptors : 6.0
Num. H-bond donors : 2.0
Molar Refractivity : 142.66
TPSA : 105.17 Ų

Pharmacokinetics

GI absorption : Low
BBB permeant : No
P-gp substrate : Yes
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : Yes
CYP2D6 inhibitor : Yes
CYP3A4 inhibitor : Yes
Log Kp (skin permeation) : -5.55 cm/s

Lipophilicity

Log Po/w (iLOGP) : 3.85
Log Po/w (XLOGP3) : 5.44
Log Po/w (WLOGP) : 5.79
Log Po/w (MLOGP) : 3.4
Log Po/w (SILICOS-IT) : 4.45
Consensus Log Po/w : 4.59

Druglikeness

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

Water Solubility

Log S (ESOL) : -5.68
Solubility : 0.00106 mg/ml ; 0.00000207 mol/l
Class : Moderately soluble
Log S (Ali) : -7.4
Solubility : 0.0000201 mg/ml ; 0.0000000394 mol/l
Class : Poorly soluble
Log S (SILICOS-IT) : -7.01
Solubility : 0.0000498 mg/ml ; 0.0000000975 mol/l
Class : Poorly soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 3.0
Synthetic accessibility : 4.83

Safety of [ 201003-48-7 ]

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

Application In Synthesis of [ 201003-48-7 ]

* 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 [ 201003-48-7 ]

[ 201003-48-7 ] Synthesis Path-Downstream   1~3

  • 1
  • [ 35661-60-0 ]
  • [ 201003-48-7 ]
  • [ 1253282-31-3 ]
  • [ 1433975-21-3 ]
  • [ 71989-31-6 ]
  • [ 71989-33-8 ]
  • [ 79990-15-1 ]
  • [ 76-05-1 ]
  • [ 142994-19-2 ]
  • [ 142994-45-4 ]
  • [ CAS Unavailable ]
YieldReaction ConditionsOperation in experiment
Stage #1: N-(9-fluorenylmethoxycarbonyl)-D-alanine With benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine In 1-methyl-pyrrolidin-2-one; dichloromethane at 20℃; Stage #2: With piperidine In N,N-dimethyl-formamide for 0.416667h; Stage #3: Fmoc-Leu-OH; Fmoc-L-Lys(iPr,Boc)-OH; 9-fluorenylmethyloxycarbonyl-N(4)-(L-hydroorotyl)-4-aminophenylalanine; 9-fluorenylmethyloxycarbonyl-N(4)-(t-butylcarbamoyl)-D-4-aminophenylalanine; Fmoc-Pro-OH; Fmoc-Ser(tBu)-OH; N-(9-fluorenylmethoxycarbonyl)-D-alanine; trifluoroacetic acid; 9-fluorenylmethyloxycarbonyl-D-4-chlorophenylalanine; (R)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-3-(pyridin-3-yl)propanoic acid Further stages;
  • 2
  • [ 35661-60-0 ]
  • [ 201003-48-7 ]
  • [ 1253282-31-3 ]
  • [ 1433975-21-3 ]
  • [ 71989-31-6 ]
  • [ 71989-33-8 ]
  • [ 108-24-7 ]
  • [ 79990-15-1 ]
  • [ 76-05-1 ]
  • [ 138774-94-4 ]
  • [ 142994-19-2 ]
  • [ 142994-45-4 ]
  • [ 2089022-30-8 ]
YieldReaction ConditionsOperation in experiment
Stage #1: N-(9-fluorenylmethoxycarbonyl)-D-alanine With benzotriazol-1-ol; diisopropyl-carbodiimide In N,N-dimethyl-formamide at 25℃; for 1h; Stage #2: With pyrrolidine In N,N-dimethyl-formamide for 0.0833333h; Stage #3: Fmoc-Leu-OH; Fmoc-L-Lys(iPr,Boc)-OH; 9-fluorenylmethyloxycarbonyl-N(4)-(L-hydroorotyl)-4-aminophenylalanine; 9-fluorenylmethyloxycarbonyl-N(4)-(t-butylcarbamoyl)-D-4-aminophenylalanine; Fmoc-Pro-OH; Fmoc-Ser(tBu)-OH; acetic anhydride; trifluoroacetic acid; N-[(9-fluorenyl)methoxycarbonyl]-3-(2-naphthyl)-D-alanine; 9-fluorenylmethyloxycarbonyl-D-4-chlorophenylalanine; (R)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-3-(pyridin-3-yl)propanoic acid Further stages; 1-7 Example- 1: Charged 50 g of Rink amide AM resin and 500 mF of DMF into the Peptide vessel. Stirred the resin for 10 min and solvent is removed by applying vacuum. For swelling of resin charged 500 mF of DMF and allowed resin to stir for 45 min. Removed solvent by applying vacuum. Charged solution of 2% of Pyrrolidine in DMF into peptide vessel and stir for 10 min to deprotect the Fmoc of Resin. Kaiser test indicated complete deprotection.Coupling of Amino acid: Charged solution of 32.68 g of Fmoc-D-Ala-OH, 16.08 g of HOBt.PhO and 16.44 mF of DIPC into 500 mF of DMF into peptide vessel and stirred for 1 hr at 25+5°C. Kaiser test indicated complete coupling of N-protected amino acid.Deprotection of Amino acid: Charged 500 mF of solution of 2% Pyrrolidine in DMF into peptide vessel and stirred for 5 min. Removed the solvent by applying vacuum and repeated second deprotection for 10 min. Washed the resin with 4x500 mF of DMF and tested resin bead for deprotection. Repeated above coupling and deprotection procedure for sequential loading of Fmoc-Pro-OH, Fmoc-ILys(Boc)-OH, Fmoc-Leu-OH, Fmoc-D-4Aph(tBu-cbm)-OH, Fmoc-L-4Aph(L-Hor)- OH, Fmoc-Ser(tBu)-OH, Fmoc-D-3-Pal-OH, Fmoc-D-Phe(4-Cl)-OH, Fmoc-D-2-Nal-OH.Acetylation: After deprotection of Fmoc-D-2-Nal-OH, charged solution of 12.5 mL of acetic anhydride and 10 mL of DIPEA in 500 mL of DMF into peptide vessel and stirred for 30 min. Removed the solvent by applying vacuum. Washed the resin with 3x500 mL of DML and tested resin bead for coupling.Cleavage of Degarelix form Resin: Charged 500 mL of TLA into a reaction vessel and cooled to l5+5°C. Charged resin slowly into the reaction vessel and stirred for 30 to 40 hrs at 25+5°C. Liltered the resin and the filtrate was concentrated under vacuum at 25+5°C. Charged concentrated residue into pre-chilled Di-isopropyl ether and stir for 1 hr at 25+5°C. Liltered the solid under vacuum and washed the solid with Di-isopropyl ether and the wet cake was dried under vacuum for 3 hrs. at 30°C. Obtained weight of Degarelix crude is between 80g to 90g. (purity by HPLC: 88.04%)
  • 3
  • [ 35661-60-0 ]
  • [ 201003-48-7 ]
  • [ 1253282-31-3 ]
  • [ 1433975-21-3 ]
  • [ 71989-31-6 ]
  • [ 71989-33-8 ]
  • [ 1260594-61-3 ]
  • [ 108-24-7 ]
  • [ 79990-15-1 ]
  • [ 142994-19-2 ]
  • [ 142994-45-4 ]
  • [ 934016-19-0 ]
YieldReaction ConditionsOperation in experiment
Stage #1: N-(9-fluorenylmethoxycarbonyl)-D-alanine With benzotriazol-1-ol; diisopropyl-carbodiimide In N,N-dimethyl-formamide at 0 - 10℃; for 2h; Stage #2: With 3-azapentane-1,5-diamine In N,N-dimethyl-formamide for 0.5h; Stage #3: Fmoc-Leu-OH; Fmoc-L-Lys(iPr,Boc)-OH; 9-fluorenylmethyloxycarbonyl-N(4)-(L-hydroorotyl)-4-aminophenylalanine; 9-fluorenylmethyloxycarbonyl-N(4)-(t-butylcarbamoyl)-D-4-aminophenylalanine; Fmoc-Pro-OH; Fmoc-Ser(tBu)-OH; 9-fluorenylmethyloxycarbonyl-D-2-naphthylalanine; acetic anhydride; 9-fluorenylmethyloxycarbonyl-D-4-chlorophenylalanine; (R)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-3-(pyridin-3-yl)propanoic acid Further stages; 1-12 Step 1 Rink Amide Resin Activation Fmoc-Rink amide AM resin (0.5 g) was placed in a peptide vessel and the resin was washed with 5 ml DMF 2 times and kept in DMF (5 ml) for 45 min and the solvent was then removed by applying vacuum. The washed resin was then deprotected with 5% diethylenetriamine in DMF 5 ml for 15 min. The vessel was emptied by applying vacuum and treated with 5% diethylenetriamine in DMF (5 ml) for 15 min. The vessel was emptied by applying vacuum and the resin was washed with DMF (5 ml). The vessel was further washed with methanol (5 ml*2 times) and DMF (5 ml*2 times). A solution of 0.326 gm Fmoc-Ala-OH (3.0 eq), 0.14 gm HOBT.H2O (3.0 eq) and 0.165 ml diisopropylcarbodimide (3.0 eq) was dissolved in DMF at 0-10° C. and allowed to activate for 10 min. This solution was charged into the peptide vessel, stirred for 2 hrs. and deprotected with 5% diethylenetriamine in DMF (5 ml) for 15 min. The vessel was emptied by applying vacuum and a second treatment 5% diethylenetriamine in DMF 5 ml for 15 min. The vessel was emptied by applying vacuum and the resin was washed with DMF (5 ml). The vessel was further washed with methanol (5 ml*2 times) and DMF (5 ml*2 times). Step 2 (0104) A solution of 0.354 gm Fmoc-Pro-OH (3.0 eq), 0.14 gm HOBT.H2O (3.0 eq) and 0.165 ml diisopropylcarbodimide (3.0 eq) was dissolved in DMF at 0-10° C. and allowed to activate for 10 min. This solution was then charged into the peptide vessel, stirred for 2 hrs. and washed with 5 ml DMF (4 times). Then it was deprotected with 5% diethylenetriamine in DMF 5 ml for 15 min. The vessel was emptied by applying vacuum and a second treatment 5% diethylenetriamine in DMF 5 ml for 15 min. The vessel was emptied by applied vacuum and the resin washed with DMF (5 ml). The vessel was further washed with methanol (5 ml*2 times) and DMF (5 ml*2 times). (0105) Step 3 (0106) A solution of 0.536 gm Fmoc-Lys (ipr,Boc)-OH (3.0 eq), 0.14 gm HOBT.H2O (3.0 eq) and 0.165 ml diisopropylcarbodimide (3.0 eq) was dissolved in DMF at 0-10° C. and allowed to activate for 10 min and this solution charged into peptide vessel , stirred for 2 hrs., and washed with 5 ml DMF 4 times, and deprotected with 5% diethylenetriamine in DMF 5 ml for 15 min. The vessel was emptied by applying a vacuum and a second treatment 5% diethylenetriamine in DMF 5 ml for 15 min. The vessel was emptied by applied vacuum and the resin washed with DMF (5 ml). The vessel was further washed with methanol (5 ml*2 times) and DMF (5 ml*2 times). (0107) Step 4 (0108) A solution of 0.371 gm Fmoc-Leu-OH (3.0 eq), 0.14 gm HOBT.H2O (3.0 eq) and 0.165 ml diisopropylcarbodimide (3.0 eq) was dissolved in DMF at 0-10° C. and allowed to activate for 10 min and this solution charged into a peptide vessel, stirred for 2 hrs., washed with 5 ml DMF 4 times, and deprotected with 5% diethylenetriamine in DMF 5 ml for 15 min. The vessel was emptied by applying a vacuum and second treatment 5% diethylenetriamine in DMF 5 ml for 15 min. The vessel was emptied by applied vacuum and resin washed with DMF (5 ml). The vessel was further washed with methanol (5 ml*2 times) and DMF (5 ml*2 times). (0109) Step 5 (0110) A solution of 0.351 gm Fmoc-DAph(tBuCbm)-OH (2.0 eq),0.107 gm HOBT.H2O (2.0 eq) and 0.11 ml diisopropylcarbodimide (2.0 eq) was dissolved in DMF at 0-10° C. and allowed to activate for 10 min and this solution charged into the peptide vessel, stirred for 2 hrs., washed with 5 ml DMF 4 times, and deprotected with 5% diethylenetriamine in DMF 5 ml for 15 min. The vessel was emptied by applying a vacuum and a second treatment of 5% diethylenetriamine in DMF 5 ml for 15 min. The vessel was emptied by applying a vacuum and the resin washed with DMF (5 ml). the vessel was further washed with methanol (5 ml*2 times) and DMF (5 ml*2 times). (0111) Step 6 (0112) A solution of 0.379 gm Fmoc-Aph(Hor)-OH (2.0 eq),0.107 gm HOBT.H2O (2.0 eq) and 0.11 ml diisopropylcarbodimide (2.0 eq) was dissolved in DMF at 0-10° C. and allowed to activate for 10 min and this solution charged into the peptide vessel, stirred for 2 hrs. and deprotected with 5% diethylenetriamine in DMF 5 ml for 15 min. The vessel was emptied by applying a vacuum and a second treatment 5% diethylenetriamine in DMF 5 ml for 15 min. The vessel was emptied by applying a vacuum and the resin washed with DMF (5 ml). The vessel was further washed with methanol (5 ml*2 times) and DMF (5 ml*2 times). (0113) Step 7 (0114) A solution of 0.402 gm Fmoc-Ser(tBu)-OH (3.0 eq),0.14 gm HOBT.H2O (3.0eq) and 0.165 ml diisopropylcarbodimide (3.0 eq) was dissolved in DMF at 0-10° C. and allowed to activate for 10 min and this solution charged into peptide vessel, stirred for 2 hrs., washed with 5 ml DMF 4 times, and deprotected with 5% diethylenetriamine in DMF 5 ml for 15 min. The vessel was emptied by applying a vacuum and a second treatment 5% diethylenetriamine in DMF 5 ml for 15 min. The vessel was emptied by applying a vacuum and the resin washed with DMF (5 ml). The vessel was further washed with methanol (5 ml*2 times) and DMF (5 ml*2 times). (0115) Step 8 (0116) A solution of 0.407 gm Fmoc-D-3-Pal-OH (3.0 eq), 0.14 gm HOBT.H2O (3.0 eq) and 0.165 ml diisopropylcarbodimide (3.0 eq) was dissolved in DMF at 0-10° C. and allowed to activate for 10 min and this solution charged into peptide vessel, stirred for 2 hrs., and washed with 5 ml DMF 4 times and deprotected with 5% diethylenetriamine in DMF 5 ml for 15 min. The vessel was emptied by applying a vacuum and a second treatment 5% diethylenetriamine in DMF 5 ml for 15 min. The vessel was emptied by applying a vacuum and the resin washed with DMF (5 ml). A vessel was further washed with methanol (5 ml*2 times) and DMF (5 ml*2 times). (0117) Step 9 (0118) A solution of 0.442 gm Fmoc-D-Phe (4-Cl)-OH (3.0 eq), 0.14 gm HOBT.H2O (3.0eq) and 0.165 ml diisopropylcarbodimide (3.0 eq) was dissolved in DMF at 0-10° C. and allowed to activate for 10 min and this solution charged in to peptide vessel, stirred for 2 hrs. washed with 5 ml DMF 4 times, and deprotected with 5% diethylenetriamine in DMF 5 ml for 15 min. The vessel was emptied by applying a vacuum and a second treatment 5% diethylenetriamine in DMF 5 ml for 15 min. The vessel was emptied by applying a vacuum and the resin washed with DMF (5 ml). The vessel was further washed with methanol (5 ml*2 times) and DMF (5 ml*2 times). (0119) Step 10 (0120) A solution of 0.459 gm Fmoc-D-2-Nal-OH (3.0 eq), 0.14 gm HOBT.H2O (3.0 eq) and 0.165 ml diisopropylcarbodimide (3.0 eq) was dissolved in DMF at 0-10° C. and allowed to activate for 10 min and this solution charged into peptide vessel, stirred for 2 hrs., washed with 5 ml DMF 4 times, and deprotected with 5% diethylenetriamine in DMF 5 ml for 15 min. The vessel was emptied by applying a vacuum and second treatment 5% diethylenetriamine in DMF 5 ml for 15 min. The vessel was emptied by applying a vacuum and resin washed with DMF (5 ml). A vessel was further washed with methanol (5 ml*2 times) and DMF (5 ml*2 times). (0121) Step 11 (0122) Acetic anhydride (0.125 gm) was dissolved in dichloromethane (MDC) at 0-10° C. and charged into peptide vessel. The vessel was stirred for 3 hours and washed with dichloromethane (MDC-5 ml*4 times) and Methyltertiarybutylether (MTBE-5 ml*2 times) simultaneously. (0123) Step 12 (0124) TFA (5 ml) was taken in RBF and cooled to 0-10° C. Above the resin bed was then charged into TFA solution. Reaction mixture was then stirred for 24 hrs. at room temperature. Solution was filtered and then washed with TFA (1 ml). Filtrate ml was then distilled out up to one volume under vacuum and below 35° C. Methyltertiarybutylether (MTBE) (30 ml) was taken in another RBF and cooled to 0-10° C. Residue was then charged in this solution and then stirred for 1 hr. and filtered. The compound was dried under vacuum at 35° C. for 6-8 hr. Purity of the crude was about 85%-95%. The compound was further purified using preparative HPLC to get highly pure compound, greater than about 85%-95%.
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