Home Cart 0 Sign in  

[ CAS No. 13734-34-4 ] {[proInfo.proName]}

,{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]}
Chemical Structure| 13734-34-4
Chemical Structure| 13734-34-4
Structure of 13734-34-4 * Storage: {[proInfo.prStorage]}
Cart0 Add to My Favorites Add to My Favorites Bulk Inquiry Inquiry Add To Cart

Quality Control of [ 13734-34-4 ]

Related Doc. of [ 13734-34-4 ]

Alternatived Products of [ 13734-34-4 ]

Product Details of [ 13734-34-4 ]

CAS No. :13734-34-4 MDL No. :MFCD00002663
Formula : C14H19NO4 Boiling Point : -
Linear Structure Formula :- InChI Key :ZYJPUMXJBDHSIF-NSHDSACASA-N
M.W : 265.31 Pubchem ID :77857
Synonyms :

Safety of [ 13734-34-4 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P280-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H332-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 13734-34-4 ]

* 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 [ 13734-34-4 ]

[ 13734-34-4 ] Synthesis Path-Downstream   1~85

  • 1
  • [ 24424-99-5 ]
  • [ 17585-69-2 ]
  • [ 13734-34-4 ]
  • 3
  • [ 13734-34-4 ]
  • [ 29390-67-8 ]
  • [ 131176-22-2 ]
  • 5
  • [ 13734-34-4 ]
  • [ 16115-68-7 ]
  • [ 136497-23-9 ]
  • 7
  • [ 13734-34-4 ]
  • [ 6038-19-3 ]
  • [ 192310-93-3 ]
  • 9
  • [ 13734-34-4 ]
  • [ 72784-43-1 ]
  • Boc-Phe-Ac3c-OMe [ No CAS ]
  • 10
  • [ 13734-34-4 ]
  • [ 37993-32-1 ]
  • [ 174077-47-5 ]
  • 11
  • [ 13734-34-4 ]
  • [ 5382-17-2 ]
  • [ 186431-51-6 ]
  • 12
  • [ 63-91-2 ]
  • [ 13734-34-4 ]
  • [ 84624-28-2 ]
  • {(S)-5-((S)-2-Amino-3-phenyl-propionylamino)-5-[(S)-1-((S)-1-carbamoyl-2-phenyl-ethylcarbamoyl)-2-phenyl-ethylcarbamoyl]-pentyl}-carbamic acid 9H-fluoren-9-ylmethyl ester [ No CAS ]
  • 13
  • [ 13734-34-4 ]
  • [ 33209-01-7 ]
  • [(S)-1-((1S,2R)-1-Carbamoyl-2-hydroxy-propylcarbamoyl)-2-phenyl-ethyl]-carbamic acid tert-butyl ester [ No CAS ]
  • 14
  • [ 103-82-2 ]
  • [ 13734-34-4 ]
  • [ 100-39-0 ]
  • [ 73724-45-5 ]
  • (S)-3-[(S)-1-(Benzylamino-methyl)-2-phenyl-ethylamino]-2-phenethylamino-propan-1-ol [ No CAS ]
  • 15
  • [ 103-82-2 ]
  • [ 13734-34-4 ]
  • [ 100-39-0 ]
  • [ 135112-28-6 ]
  • <i>N</i>1-[1-(benzylamino-methyl)-2-phenyl-ethyl]-<i>N</i>2-phenethyl-pentane-1,2-diamine [ No CAS ]
  • 16
  • [ 103-82-2 ]
  • [ 13734-34-4 ]
  • [ 73724-45-5 ]
  • [ 74-88-4 ]
  • (S)-3-((S)-1-Methylaminomethyl-2-phenyl-ethylamino)-2-phenethylamino-propan-1-ol [ No CAS ]
  • 17
  • [ 103-82-2 ]
  • [ 13734-34-4 ]
  • [ 135112-28-6 ]
  • [ 74-88-4 ]
  • <i>N</i>1-(1-methylaminomethyl-2-phenyl-ethyl)-<i>N</i>2-phenethyl-pentane-1,2-diamine [ No CAS ]
  • 18
  • [ 13734-34-4 ]
  • [ 13515-95-2 ]
  • N-(tert-Butoxycarbonyl)-L-phenylalanyl-Nα-L-lysine methyl ester [ No CAS ]
  • 19
  • [ 13139-15-6 ]
  • [ 13734-34-4 ]
  • [ 128797-22-8 ]
  • [ 35897-34-8 ]
  • Boc-Gly-OH, Boc-Lys(Fmoc)-OH, Boc-Pro-OH, Boc-Lys(Fmoc)-Pac-resin [ No CAS ]
  • [ 77739-20-9 ]
  • 20
  • [ 13734-34-4 ]
  • [ 20866-48-2 ]
  • [ 5241-66-7 ]
  • [ 35899-43-5 ]
  • Boc-Leu-OH, Boc-Met-OH, Boc-Asp(benzyl)-OH [ No CAS ]
  • [ 119975-64-3 ]
  • 21
  • [ 15761-39-4 ]
  • [ 13734-34-4 ]
  • [ 53462-50-3 ]
  • [ 35899-43-5 ]
  • Boc-Tyr(δ-Br-Z) or Boc-Tyr(2,6-Cl2Bzl), Boc-Val, Boc-Arg, Boc-Sar [ No CAS ]
  • [ 135145-71-0 ]
  • 22
  • [ 4530-20-5 ]
  • [ 13139-15-6 ]
  • [ 13734-34-4 ]
  • [ 5241-66-7 ]
  • Boc-Gln, Boc-Pro, Boc-Lys(2-ClZ), Boc-Arg(Tos) [ No CAS ]
  • [ 79820-95-4 ]
  • 23
  • [ 13734-41-3 ]
  • [ 4587-33-1 ]
  • [ 13734-34-4 ]
  • [ 76757-91-0 ]
  • Boc-Cys(Bzl), β-(benzylthio)-β,β-pentamethylenepropionic acid, ethylenediamine [ No CAS ]
  • <(β-benzylthio)-β,β-pentamethylenepropionyl>-L-Tyr(Et)-Phe-Val-Asn-Cys(Bzl)-NH(CH2)2NH2 [ No CAS ]
  • 24
  • [ 13734-41-3 ]
  • [ 13734-34-4 ]
  • [ 39608-31-6 ]
  • [ 13836-37-8 ]
  • 1.) Boc-Val-His(Tos)-Pro-Phe-resin ester [ No CAS ]
  • [ 88180-45-4 ]
  • 25
  • [ 4530-20-5 ]
  • [ 13726-67-5 ]
  • [ 13734-34-4 ]
  • [ 13726-76-6 ]
  • Boc-D-Tyr [ No CAS ]
  • (cyclo)-D-Tyr1-Arg2-Gly3-Asp4-Phe5-Gly6 [ No CAS ]
  • 26
  • [ 13139-15-6 ]
  • [ 13734-34-4 ]
  • [ 13836-37-8 ]
  • [ 53100-44-0 ]
  • N-Boc-Pro-OH [ No CAS ]
  • p-Glu-Phe-Leu-Phe-Arg-Pro-Arg-OH [ No CAS ]
  • 27
  • [ 13139-15-6 ]
  • [ 13734-34-4 ]
  • [ 13836-37-8 ]
  • [ 53100-44-0 ]
  • N-Boc-Pro-OH; N-Boc-Asn-OH [ No CAS ]
  • p-Glu-Phe-Leu-Phe-Arg-Pro-Arg-Asn-NH2 [ No CAS ]
  • 28
  • [ 13734-41-3 ]
  • [ 13734-34-4 ]
  • [ 117014-32-1 ]
  • [ 176486-63-8 ]
  • Boc-His(Bom), Boc-Tyr(2-Cl-Bzl), Boc-Arg(Tos), Boc-Sar [ No CAS ]
  • C47H64N14O11 [ No CAS ]
  • 29
  • [ 13734-41-3 ]
  • [ 13734-34-4 ]
  • [ 123417-18-5 ]
  • [ 176486-63-8 ]
  • Boc-His(Bom), Boc-Tyr(2-Cl-Bzl), Boc-Arg(Tos), Boc-Sar [ No CAS ]
  • Sar-Arg-Val-Tyr-cyclo(Glu-His-Apt)-Phe [ No CAS ]
  • 30
  • [ 4530-20-5 ]
  • [ 13734-34-4 ]
  • [ 104323-41-3 ]
  • [ 62129-39-9 ]
  • Boc-D-Pen(p-MeBzl), Boc-Tyr(2,6-Cl2Bzl) [ No CAS ]
  • (S)-2-{(R)-2-[(S)-2-(2-{(S)-2-[(S)-2-Amino-3-(4-hydroxy-phenyl)-propionylamino]-3-mercapto-3-methyl-butyrylamino}-acetylamino)-3-(4-bromo-phenyl)-propionylamino]-3-mercapto-3-methyl-butyrylamino}-3-phenyl-propionic acid [ No CAS ]
  • 31
  • [ 13734-34-4 ]
  • [ 79416-27-6 ]
  • [ 321837-83-6 ]
YieldReaction ConditionsOperation in experiment
83.2% With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 24℃; for 6h; In a 50 mL round bottom flask,<strong>[79416-27-6]5-aminolevulinic acid methyl ester hydrochloride</strong> (1.0 g, 5.5 mmol),Boc-L-phenylalanine (1.46 g, 5.5 mmol),HBTU (1.7 g, 4.49 mmol) was dissolved in DMF (10 mL) followed by DIPEA (2.0 mL, 11.5 mmol) was added and stirred at 24 ° C for 6h. The solvent was concentrated under reduced pressure, and the residue was separated by silica gel column chromatography. The eluent was methylene chloride:Methanol (v / v = 50: 1) to give a white solidMethyl 5 - ((2'-tert-butyloxycarbonylamino) -L-phenylpropionyl) amino-4-oxopentanoate1.79 g, yield 83.2percent.
  • 32
  • [ 15761-38-3 ]
  • [ 13734-34-4 ]
  • [ 40298-71-3 ]
  • [ 131570-56-4 ]
  • Boc-Arg(Tos)Boc-Trp(For) [ No CAS ]
  • Tyr-c[β-Asp-Ala-DPhe-Arg-Trp-Asn-Ala-Phe-Dpr]-Tyr-NH2 [ No CAS ]
  • 33
  • [ 15761-38-3 ]
  • [ 13734-34-4 ]
  • [ 40298-71-3 ]
  • [ 131570-56-4 ]
  • Boc-Arg(Tos)Boc-Trp(For) [ No CAS ]
  • Tyr-c[β-Asp-His-Ala-Arg-Trp-Asn-Ala-Phe-Dpr]-Tyr-NH2 [ No CAS ]
  • 34
  • [ 13734-34-4 ]
  • [ 142-64-3 ]
  • {1-benzyl-2-[4-(2-<i>tert</i>-butoxycarbonylamino-3-phenyl-propionyl)-piperazin-1-yl]-2-oxo-ethyl}-carbamic acid <i>tert</i>-butyl ester [ No CAS ]
  • 35
  • [ 13734-34-4 ]
  • [ 24629-25-2 ]
  • [(1S)-[(1S,2S)-1-hydroxymethyl-2-methylbutylcarbamoyl]-2-phenylethyl]carbamic acid tert-butyl ester [ No CAS ]
  • 36
  • [ 4488-22-6 ]
  • [ 13734-34-4 ]
  • {1-[2'-(2-<i>tert</i>-butoxycarbonylamino-3-phenyl-propionylamino)-[1,1']binaphthalenyl-2-ylcarbamoyl]-2-phenyl-ethyl}-carbamic acid <i>tert</i>-butyl ester [ No CAS ]
  • {1-[2'-(2-<i>tert</i>-butoxycarbonylamino-3-phenyl-propionylamino)-[1,1']binaphthalenyl-2-ylcarbamoyl]-2-phenyl-ethyl}-carbamic acid <i>tert</i>-butyl ester [ No CAS ]
  • 37
  • [ 13734-34-4 ]
  • [ 25808-30-4 ]
  • [1-(cyanomethyl-methyl-carbamoyl)-2-phenyl-ethyl]-carbamic acid <i>tert</i>-butyl ester [ No CAS ]
  • 39
  • [ 13734-34-4 ]
  • [ 39994-75-7 ]
  • [ 500220-28-0 ]
  • 40
  • [ 13734-34-4 ]
  • [ 17585-69-2 ]
  • 43
  • [ 86-59-9 ]
  • [ 13734-34-4 ]
  • 1N-(N-(8-quinoline-carbonyl)-L-phenylalaninyl)amino-3-[3-(2-pyridyl)phenylacetyl]amino-2-butanone [ No CAS ]
YieldReaction ConditionsOperation in experiment
a 1N-(N-(8-Quinoline-carbonyl)-L-phenylalaninyl)amino-3-[3-(2-pyridyl)phenylacetyl]amino-2-butanone Following the procedure of Example 1(a-e), (g-i) except substituting "8-quinoline-carboxylic acid" for "2-thianaphthenylcarboxylic acid" and "Boc-L-phenylalanine" for "Boc-L-leucine" gave the title compound: MS (ES+) 600.2 (M+H+).
  • 44
  • [ 13734-34-4 ]
  • [ 64051-79-2 ]
  • [(1S)-Benzyl-2-((3RS)-hydroxy-piperidin-1-yl)-2-oxo-ethyl]-carbamic acid tert-butyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
EXAMPLE 79b [(1S)-Benzyl-2-((3RS)-hydroxy-piperidin-1-yl)-2-oxo-ethyl]-carbamic acid tert-butyl ester BOC-L-phenylalanine (8.17 g, 30.8 mmol) and <strong>[64051-79-2]3-hydroxypiperidine hydrochloride</strong> (4.24 g, 30.8 mmol) were coupled according to procedure A, giving the title compound as an oil which was used without further purification. Yield 7.79 g, 73%.
Example 79b [(1S)-Benzyl-2-((3RS)-hydroxy-piperidin-1-yl)-2-oxo-ethyl]-carbamic acid tert-butyl ester BOC-L-Phenylalanine (8.17 g, 30.8 mmol) and <strong>[64051-79-2]3-hydroxypiperidine hydrochloride</strong> (4.24 g, 30.8 mmol) were coupled according to procedure A, giving the title compound as an oil which was used without further purification. Yield 7.79 g, 73 %.
  • 46
  • [ 13734-34-4 ]
  • [ 2791-84-6 ]
  • [ 176448-92-3 ]
  • 47
  • [ 13734-34-4 ]
  • [ 66491-03-0 ]
  • [ 1094107-22-8 ]
YieldReaction ConditionsOperation in experiment
53% To a solution of 7-amino-3,4- dihydroisoquinolin-l(2H)-one (0.1 g, 0.617 mmol), (S)-2-(tert- butoxycarbonylamino)-3-phenylpropanoic acid (0.164 g, 0.617 mmol) in pyridine (3 mL) cooled in ice/acetone bath, was added POCI3 (0.057 mL, 0.617 mmol). After 1 h, the deep red reaction was concentrated and quenched with 0. IN HCl (10 mL) and ethyl acetate (30 mL). The organic layer was washed with sat'd nuaHCtheta3 (10 mL), brine (10 mL) and dried (MgSO4). Filtration and concentration afforded 63A (0.135 g, 53%) as a yellow solid. LCMS m/z 408.2.(M-H).
  • 48
  • [ 15761-39-4 ]
  • [ 13734-41-3 ]
  • [ 13139-16-7 ]
  • [ 13139-15-6 ]
  • [ 13734-34-4 ]
  • [ 82732-07-8 ]
  • [ 1187223-34-2 ]
  • 49
  • [ 15761-39-4 ]
  • [ 13734-41-3 ]
  • [ 13139-16-7 ]
  • [ 13139-15-6 ]
  • [ 13734-34-4 ]
  • [ 82732-07-8 ]
  • [ 1187223-35-3 ]
  • 50
  • [ 15761-39-4 ]
  • [ 13734-41-3 ]
  • [ 13139-16-7 ]
  • [ 13139-15-6 ]
  • [ 13734-34-4 ]
  • [ 82732-07-8 ]
  • [ 1187223-36-4 ]
  • 51
  • [ 13734-34-4 ]
  • [ 124-41-4 ]
  • [ 3034-48-8 ]
  • [ 1235447-18-3 ]
  • 52
  • [ 13734-34-4 ]
  • [ 101-79-1 ]
  • C26H27ClN2O4 [ No CAS ]
  • 53
  • [ 13734-34-4 ]
  • [ 77128-73-5 ]
  • C24H29N3O4 [ No CAS ]
  • 54
  • [ 13734-34-4 ]
  • [ 77128-73-5 ]
  • [ 1404615-77-5 ]
YieldReaction ConditionsOperation in experiment
The Fmoc Sieber resin (670 mg, 0.45 mmol) was swollen in DMF then treated with 20percent piperidine in DMF (2.5 ml). After several washings with DMF, Fmoc-Sar-OH (280 mg, 0.9 mmol, 2 equiv), HOBt (135 mg, 0.9 mmol, 2 equiv) and DIC (140 muL, 0.9 mmol, 2 equiv) were added. The resin was vortexed at room temperature for 30 min before being washed with DMF (.x.6) and treated with 20percent piperidine in DMF (2.5 ml) for 30 min. This step was repeated once. Then Boc-Phe-OH (240 mg, 0.9 mmol, 2 equiv), HOBt (135 mg, 0.9 mmol, 2 equiv) and DIC (140 muL, 0.9 mmol, 2 equiv) were added and the mixture was shaken at room temperature for 30 min. The resin was washed with DMF (.x.6), MeOH (.x.6), DMF (.x.6), CH2Cl2 (.x.6) and Et2O (.x.6). Cleavage was performed by treatment of resins with a mixture of distilled CH2Cl2/TFA (98:2, v/v) at room temperature for 10 min (.x.6). The TFA was neutralized by pyridine then the mixture was concentrated under high vaccum. Filtrate was evaporated and gave 0.33 mmol of dipeptide 5a.
  • 55
  • [ 13734-34-4 ]
  • [ 77128-73-5 ]
  • [ 102523-58-0 ]
YieldReaction ConditionsOperation in experiment
General procedure: 2-Cl-Chlorotrityl resin (316 mg, 0.57 mmol) was rinsed with distilled CH2Cl2 (.x.3) and swollen in distilled CH2Cl2. A solution of N-Fmoc-Sar-OH (355 mg, 1.14 mmol, 2 equiv) and DIPEA (0.6 mL, 3.42 mmol, 6 equiv) was added onto the resin. The mixture was gently stirred for 4 h at room temperature. Solvent was removed by filtration and the resin was washed with distilled CH2Cl2 (.x.4), MeOH (.x.2), DMF (.x.2), distilled CH2Cl2 (.x.2) and Et2O (.x.2). After drying, the N-Fmoc-Sar resin was swollen in distilled DCM and deprotected using DMF/piperidine (3:1). The mixture is stirred at room temperature for 20 min then the solvent was removed by filtration and the resin washed with DMF (3.x.6 min). This step was repeated once. The loading was determined by UV spectrometry: 0.74 mmol. A mixture of Boc-Phe-OH (450 mg, 1.7 mmol, 5 equiv), Benzotriazole-1-yl-oxy-tris-(dimethylamino)-phosphonium hexa-fluorophosphate (BOP) (752 mg, 1.7 mmol, 5 equiv), HOBt (230 mg, 1.7 mmol, 5 equiv) and DIPEA (891 muL, 5.1 mmol, 15 equiv) in DMF (5 mL) was added to the Sar resin and stirred for 30 min at room temperature. The solvent was removed by filtration, the resin was rinsed with DMF (.x.2) and the coupling step was repeated under the same conditions. After filtration, the resin was washed with DMF (3.x.6 min) and distilled CH2Cl2 (1.x.6 min). Cleavage was performed by treatment of resins with a mixture of distillated CH2Cl2/hexafluoroisopropanol (2:3, v/v) for 2 h at room temperature. The purity was checked by HPLC and was above 90percent.
  • 56
  • [ 29331-92-8 ]
  • [ 13734-34-4 ]
  • [ 1399078-93-3 ]
YieldReaction ConditionsOperation in experiment
With dmap; dicyclohexyl-carbodiimide; In dichloromethane; at 5 - 10℃; for 6h;Product distribution / selectivity; Example 11:Preparation of N-Boc-protected phenylalanine ester of licarbazapine A solution of N-Boc phenylalnine (15 gm) and triethyl amine (11.9 gm) in dichloromethane (60 mL) was cooled to 0-5C. To the resulting solution pivaloyl chloride (6.5 mL) was added at same temperature. The reaction mass was stirred for 1 h at 20-25C and then filtered. Thus obtained filtrate was added to a solution of licarbazepine, pyridine (5.5 g), dimethylaminopyridine (1 gm) in dichloromethane (60 mL) at 20-25C. Reaction mass was stirred for 3-4 h and washed with 2% sodium bicarbonate solution (50 mL). The solvent was distilled to obtain the title compound.Example 9:Preparation of isobutyloxycarbonyl protected phenylalanine ester of licarbazapineA solution of (l-chlorocarbonyl-2-phenyl-ethyl)-carbamic acid isobutyl ester (5 gm), obtained solution in dichloromethane was added to a solution of licarbazepine (4 gm), pyridine (2.2 mL), dimethylaminopyridine (0.05 gm) and dichloromethane (60 mL) at 5-10C. Reaction mass was stirred at room temperature for 4 h and washed with water. The solvent was distilled to obtain the title compound.
Example 11 Preparation of N-Boc-Protected Phenylalanine Ester of Licarbazapine A solution of N-Boc phenylalnine (15 gm) and triethyl amine (11.9 gm) in dichloromethane (60 mL) was cooled to 0-5 C. To the resulting solution pivaloyl chloride (6.5 mL) was added at same temperature. The reaction mass was stirred for 1 h at 20-25 C. and then filtered. Thus obtained filtrate was added to a solution of licarbazepine, pyridine (5.5 g), dimethylaminopyridine (1 gm) in dichloromethane (60 mL) at 20-25 C. Reaction mass was stirred for 3-4 h and washed with 2% sodium bicarbonate solution (50 mL). The solvent was distilled to obtain the title compound.
  • 57
  • [ 13734-34-4 ]
  • [ 60719-84-8 ]
  • [ 1401206-57-2 ]
  • 58
  • [ 13734-34-4 ]
  • [ 2566-30-5 ]
  • 59
  • [ 13734-34-4 ]
  • [ 76-05-1 ]
  • [ 40353-55-7 ]
  • C22H24N4O3S*C2HF3O2 [ No CAS ]
  • 60
  • [ 13734-34-4 ]
  • [ 17585-69-2 ]
  • [ 13122-89-9 ]
YieldReaction ConditionsOperation in experiment
100% General procedure: The Nalpha terminal Boc-protected peptides were all deprotected by a mixture of TFA in CH2Cl2 1:1 at r.t. The intermediate TFA salts were used for subsequent reactions without further purification. The Nalpha Boc-protected amino acid (1.1 eq) was dissolved in DMF, then EDC (1.1 eq.), HOBt (1.1 eq.) and DIPEA (1.65 eq.) were added at 0°C. After 10min the amino acid or the intermediate peptide as TFA salt (1 eq.) was added together with DIPEA (1.65 eq.). The reaction was stirred for additional 10min at 0°C, allowed to warm at r.t. and stirred overnight. The solvent was evaporated under reduced pressure, the residue was suspended in EtOAc and washed with three portions of citric acid 5percent, NaHCO3 s.s., and brine. The organic layers were combined, dried under Na2SO4, filtered and evaporated under reduced pressure to give a crude solid.
  • 61
  • [ 13734-34-4 ]
  • [ 2577-40-4 ]
  • 62
  • [ 13734-34-4 ]
  • [ 252932-48-2 ]
  • (S)-ethyl-3-(2-(4-(tert-butoxy)-3,4-dioxo-1-phenylbutan-2-yl)hydrazinyl)-1H-pyrrole-2-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
With (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20℃; General procedure: To a solution of pyrrole amino-ester 11 (1equiv) in DCM, DIEA (2equiv), the appropriate Boc-protected amino acid (1.2equiv) and BOP (1.2equiv) are added successively. The mixture was stirred for 3-4h at room temperature. The reaction was monitored by HPLC. Once the starting material has completely disappeared, the DCM was evaporated to give a yellow solid, which was dissolved in AcOEt:water 1:1. The organic layer was washed with KHSO4 1M (2×10mL), saturated NaHCO3 (2×20mL) and brine, dried over anhydrous Na2SO4 and evaporated under vacuum to give a yellow solid. The crude product was purified by silica gel flash chromatography using methanol and dichloromethane as eluents.
  • 63
  • [ 35661-60-0 ]
  • [ 13734-34-4 ]
  • C13H19N4O5Pol [ No CAS ]
  • [ 67436-13-9 ]
  • C40H60N7O10PolS [ No CAS ]
  • 64
  • [ 13734-34-4 ]
  • C13H19N4O5Pol [ No CAS ]
  • [ 122889-11-6 ]
  • C37H47N6O10Pol [ No CAS ]
  • 65
  • [ 13734-34-4 ]
  • [ 862847-44-7 ]
  • [ 71989-38-3 ]
  • [ 71989-35-0 ]
  • 1-tert-butoxycarbonyl-N-[(9-fluorenyl)methoxycarbonyl]-D-tryptophan [ No CAS ]
  • [ 169555-95-7 ]
  • Nα-(9-fluorenylmethyloxycarbonyl)-Nγ-2,2,4,6,7-pentamethyldihydrobenzofuran-5-sulfonyl-L-arginine [ No CAS ]
  • NH2-cyclo[DLys-Arg-Phe-4Pal-DTrp-Lys(ivDde)-Thr-Tyr] [ No CAS ]
YieldReaction ConditionsOperation in experiment
29.8% Fmoc-Tyr(tBu)-OH (12 mmole, 5.51 g) was dissolved in solution of 40 mL of DCM and 20 mL of DMF. To this solution, 2-chlorotrityl resin with substitution of 1.5 mmol/g (12.135 mmole, 8.09 g) and diisopropylethylamine (36 mmol, 6.27 mL) were added. After 3 hours, the resin was filtered and washed 3 times with DMF and then DCM. The resin was then treated for 1.5 hours with 10% DIEA in MeOH. The resin was sequentially washed with DMF, DCM and MeOH and dried overnight. Substitution of the resin was determined as 0.58 mmoles/g according to 1,8-diazabicyclo[5.4.0]undec-7-ene procedure in M. Gude, et al., Lett. Pep. Sci. 9, 203. (2003). The titled peptide was prepared using Symphony synthesizer (Protein Technologies, Inc., Tucson, Ariz., USA) based on Fmoc chemistry. 0.345 g of pre-loaded Fmoc-Tyr(tBu)-2-ClTrt resin with substitution of 0.58 mmol/g was used and synthesis was carried out on a 0.2 mmol scale. The Fmoc amino acids utilized with side chain protecting groups were as follows: Fmoc-Thr(tBu)-OH, Fmoc-Lys(ivDde)-OH, Fmoc-DTrp(Boc)-OH, Fmoc-Phe-OH, <strong>[169555-95-7]Fmoc-4Pal-OH</strong>, and Fmoc-Arg(Pbf)-OH (CBL Biopharma, Boulder, Colo., USA) and Fmoc-DLys (Mtt)-OH (Chem-Impex Int'l Inc., Wood Dale, Ill., USA). The synthesizer was programmed to perform the following reaction cycles: washing with DMF; removing Fmoc protecting group with 20% piperidine in DMF for 15 minutes for the first 3 amino acids and 30 minutes for the Fmoc-DTrp(Boc)-OH through the end of the peptide; washing with DMF; and coupling with 0.9 eq. of HCTU. The resin was double coupled successively according to the sequence until peptide chain assembly was finished. The synthesis was programmed to carry out a final deprotection to remove Fmoc. The resin was mixed with 12 eq. excess of (Boc)2O and 6 eq. of DIEA in 4 mL of DMF for 2 hours, which was repeated once. An aliquot of global cleavage showed MS of 1383, which was in agreement with the calculated molecular weight of 1382.6. UPLC (5% to 80% B in 5 min, where A was 0.1% TFA in water and B was 0.1% TFA in acetonitrile) showed product of Rt=2.82. The above Boc-DLys(Mtt)-Arg(Pbf)-Phe-4Pal-DTrp(Boc)-Lys(ivDde)-Thr(tBu)-Tyr(tBu)-2-Cart resin was treated with 25 mL of cold TFA/TIS/DCM (1/5/94) for 30 minutes to afford selective cleavage. The filtrate DCM cleavage solution was neutralized by addition of 0.47 mL of TEA while in an ice bath. This was repeated twice, then three neutralized filtrates were combined and cyclization was immediately carried out using 5 eq. of PyBOP, 8 eq, of DIEA and a catalytic amount of DMF overnight. The UPLC analysis showed the retention time was shifted from 2.83 to 3.946 (gradient was 50% to 100% Buffer B in 5 minutes). MS showed 1929 (linear is 1947). The mixture was evaporated to dryness and taken into 20 mL of water and triturated to obtain an oily precipitate. The residue was mixed with 12 mL of TEA solution containing 0.8 mL of TIS, 0.8 mL of water and 0.65 g of DTT for 4 hr. The mixture was poured into 80 mL of ether and centrifuged to get precipitate. The crude cyclized peptide was dissolved in 5 mL of 50% AcOH in water and diluted 10 fold with 0.1% TFA in water. A small amount of ACN was added to make the solution clear if needed. It was loaded onto a reversed-phase preparative Luna C18 column from Phenomenex (100×21.2 mm, 100 , 5 mum). The peptide was eluted with a gradient from 20-50% B in 50 minutes, where A was 0.1% TFA in water and B was 0.1% TFA in acetonitrile. The fractions were checked on an Acquity UPLC (Waters) and fractions containing pure product were combined and lyophilized to dryness. ESI-MS analysis showed the correct product with 1365.2, in agreement with the calculated molecular weight of 1365. It generated 96 mg with 95% purity. The average yield was 29.8% based on the starting resin.
  • 66
  • [ 46460-73-5 ]
  • [ 13734-34-4 ]
  • [ 168827-59-6 ]
YieldReaction ConditionsOperation in experiment
To Boc-L-Phe-OH (65 mg, 0.25 mmol) in DMF (2 ml) were added DIEA (142 Pl, 1.02 mmol) and HATU (85 mg, 0.225 mmol). The reaction was stirred for 15 min, and then benzyl (3-aminopropyl)carbamate (50 mg, 0.20 mmol) in DMF (1 ml) was added. The reaction mixture was stirred at rt for 1 h, and then purified by preparative HPLC (20- 70percent acetonitrile-H2O containing 0.05percent TFA) to obtain (S)-benzyl (3-(2-(tert- butoxycarbonyl)amino-3-phenylpropanamido)propyl)carbamate. MS m/z 456.3(M+1 ). Retention time 1.225 min. The product thus obtained (81.2mg, 0.18 mmol) was dissolved in methanolic HCl (3M, 4 ml). The solvent was removed slowly under stream of N2, resulting in removal of the Boc group. Lyophilization from acetonitrile water mixture afforded (S)-benzyl (3-(2-amino-3-phenylpropanamido)propyl) HCl salt. MS m/z 356.2(M+1 ). Retention time 0.857 min.
  • 67
  • [ 14227-17-9 ]
  • [ 13734-34-4 ]
  • (S)-tert-butyl (1-oxo-3-phenyl-1-((2,4,6-trimethoxyphenyl)amino)propan-2-yl)carbamate [ No CAS ]
YieldReaction ConditionsOperation in experiment
48% General procedure: To the stirred solution of 1 (1 mmol) in DMF (20 mL), triethylamine (2.5 mmol) was added at 0 C and subsequently EDC.HCl(1.5 mmol) and HOBt (1 mmol) was added. The reaction mixturewas stirred for 15 min. at 0 C, after that aryl/heteroaryl amines(2) (1.1 mmol) was added and the reaction was stirred at roomtemperature for 6-8 h. The completion of the reaction was monitoredby TLC. After the completion of the reaction, crushed icewas added. The resulted precipitate was filtered, washed with coldwater and recrystallized with ethyl acetate/hexanes to yield pure3a-g.
  • 68
  • tert-butyl (S)-(1-(but-3--en-1-ylamino)-3-methyl-1-oxobutan-2-yl)carbamate [ No CAS ]
  • [ 13139-16-7 ]
  • [ 13734-34-4 ]
  • [ 1676-90-0 ]
  • [ 132327-80-1 ]
  • C68H94N8O12 [ No CAS ]
YieldReaction ConditionsOperation in experiment
1.3 g Peptide 13 was synthesized by solution phase methods using iterative coupling of Fmoc-protected amino acids. Briefly, Boc-protected homoallyl-modified valine (5a) (1.0 g, 3.7 mmol) was dissolved in a mixture of 1:1 TFA:DCM (4 mL) and allowed to stir for 4 h at room temperature upon which TLC (1:1 EtOAc:hexanes) indicated loss of starting material. The solution was diluted with CH2C12 (30 mL) and the solvent was removed in vacuo. The crude residue was dissolved in a mixture of DMF (10 mL) and N,N-diisopropylethylamine (DIEA, 5.3 mL, 30.0 mmol, 8 eq.) and allowed to stir at room temperature for 20 min. At this point, a solution of Fmoc-Gln(Trt)-OH (4.5 g, 7.4 mmol, 2 eq.), HOBt (1.0 g, 7.4 mmol, 2 eq.), HBTU (2.8 g, 7.4 mmol, 2 eq.), and DIEA (2.6 mL, 14.8 mmol, 4 eq.) in DMF (8 mL) was added to the stirring solution. The reaction mixture was heated to 50 C. and allowed to stir for 1 h. The solution was cooled to room temperature and quenched with H2O (20 mL), and to this was added EtOAc (50 mL). The organic layer was removed and washed with H2O (5×20 mL), brine (5×20 mL) and dried over MgSO4. The solvent was removed in vacuo to afford the Fmoc-protected dipeptide as a white solid which was found to be of sufficient purity to be used in subsequent reactions. The Fmoc-protected dipeptide (2.1 g, 2.7 mmol) was dissolved in a mixture of piperidine (3.0 mL, 30 mmol) in DMF (9.0 mL) and allowed to stir at room temperature for 1 h, upon which a white precipitate had formed. The precipitate was filter off, and the filtrate concentrated under reduced pressure. The crude filtrate was dissolved in EtOAc (50 mL) and extracted with H2O (5×30 mL), brine (5×30 mL) and dried over MgSO4. The solvent was removed in vacuo to afford a clear oil (1.3 g) which was used in the next step without further purification. This iterative procedure was used for subsequent amino acid couplings, at each step monitoring the conversion by LC/MS. The termination of the peptide sequence was carried out using the requisite Boc-protected amino acid. After the final coupling, the crude peptide was dissolved in EtOAc (50 mL) and washed with H2O (5×30 mL), brine (5×30 mL), and dried over MgSO4. The solvent was removed in vacuo and the product purified by column chromatography (SiO2; 1:1 DCM:EtOAc+1 to 5% MeOH) to afford a white solid (Rf=0.45 in 1:1 DCM:EtOAc+2% MeOH). 1H NMR (500 MHz, CDCl3+CD3OD) delta 7.79 (d, J=8.3 Hz, 1H), 7.66 (d, J=8.3 Hz, 1H), 7.44-7.32 (m, 3H), 7.25-7.09 (m, 17H), 5.75-5.65 (m, 1H), 5.48 (d, J=Hz, 1H), 5.04-4.91 (m, 2H), 4.37-4.35 (m, 1H), 4.33-4.24 (m, 2H), 4.19-4.14 (m, 2H), 4.02-3.97 (m, 2H), 3.79-3.77 (m, 2H), 3.56-3.54 (m, 4H), 3.21-3.19 (m, 4H), 2.57-2.25 (m, 4H), 2.22-2.14 (m, 4H), 2.07-1.92 (m, 3H), 1.85-1.80 (m, 2H), 1.43-1.42 (m, 2H), 1.41 (s, 18H) 1.38-1.35 (m, 6H), 1.13-1.11 (m, 14H), 0.89-0.79 (m, 9H); 13C NMR (126 MHz, CDCl3+CD3OD) delta 172.87, 171.95, 171.93, 171.84, 171.63, 171.18, 170.52, 155.83, 144.50 (3C), 135.36, 129.03, 128.90, 128.70 (3C), 128.67 (3C), 128.57, 128.55, 127.71 (3C), 127.68, 126.77 (3C), 126.74, 126.60, 125.43, 117.87, 116.39, 110.47, 82.01, 80.70, 73.90, 73.53, 61.91, 59.06, 59.03, 58.96, 58.92, 54.02, 38.73, 35.76, 33.36, 33.33, 29.63, 28.22 (3C), 28.13, 27.88 (3C), 27.25, 27.23, 27.22, 27.17 (3C), 25.21, 19.21, 17.59, 17.55, 15.37, 11.03. HRMS (ESI) m/z calcd for C68H94N8O12 [M+H]+: 1215.7016. found 1215.7082.
  • 69
  • [ 13734-34-4 ]
  • [ 97-09-6 ]
  • (S)-tert-butyl (1-(4-chloro-3-nitrophenylsulfonamido)-1-oxo-3-phenylpropan-2-yl)carbamate [ No CAS ]
YieldReaction ConditionsOperation in experiment
98% With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; In dichloromethane; at 20℃; for 6h; General procedure: The solution of compound 3 (3.4 g, 10 mmol) in 60 mL anhydrous DCM was reacted with <strong>[97-09-6]4-chloro-3-nitrobenzenesulfonamide</strong> (2.6 g, 11 mmol), HATU (4.56 g, 12 mmol) and ethyldiisopropylamine (2.58 g, 20 mmol) and stirred at room temperature for 6 h. Solvent was removed under reduced pressure. The reaction mixture was extracted with EtOAc. The combined organic phases were washed with 1 N citric acid and brine, dried over MgSO4, filtered and concentrated to generate the yellow oil. Finally, it was purified by silica gel chromatography (petroleum ether-ethyl acetate= 6:1, 0.2% HOAc) to generate 4.1 g compound 9a as a white powder.
75% General procedure: The solution of Boc-protected phenylalanine (1.33 g, 5 mmol) indry dichloromethane (40 mL) was treated with ethyldiisopropylamine(1.29 g, 10 mmol) under ice bath condition, after stirredfor 10 min, 2-(7-Aza-1H-benzotriazole-1-yl)-1,1,3,3-tetramethyluroniumhexafluorophosphate (2.28 g, 6 mmol) was added inand the cloudy reaction solution was stirred for 30 min, then thebenzene sulfonamide (0.86 g, 5.5 mmol) was added. After stirredfor about 6 h at room temperature. The solvent was removed andthe concentrated solution was dissolved in EtOAc. The overlyingphases were washed with 2 M citric acid, brine and dried, concentratedto yield yellow oil. Finally, the oil was purified by silica gelchromatography (Ethyl acetate: Petroleum ether = 1:3-1:5) to generatecompound 7A as a white powder-like solid.
55% With N-ethyl-N,N-diisopropylamine; HATU; In dichloromethane; at 20℃;Cooling with ice; 0.8g Boc-L-phenylalanine 5B,Dissolved in 30 mL of dichloromethane,Add 0.78g DIEA under ice bathAfter stirring for 10 minutes, add 1.37g HATU,After stirring for half an hour, 0.78 g of 3-nitro-4-chlorobenzenesulfonamide was added and the mixture was allowed to react at room temperature overnight. After the reaction was complete, the dichloromethane was removed by rotation, extracted with ethyl acetate, washed with citric acid, and dried over anhydrous magnesium sulfate. ,After concentration, column chromatography (P/E = 6:1) gave a white solid (0.8 g, 55%)
  • 70
  • [ 15761-39-4 ]
  • [ 13734-41-3 ]
  • [ 13139-15-6 ]
  • [ 15761-38-3 ]
  • [ 13726-85-7 ]
  • [ 29022-11-5 ]
  • [ 13734-34-4 ]
  • [ 13836-37-8 ]
  • 2-(decyldisulfanyl)pyridine [ No CAS ]
  • [ 23680-31-1 ]
  • [ 122889-11-6 ]
  • [ 73821-97-3 ]
  • [ 54613-99-9 ]
  • [ 25024-53-7 ]
  • fmoc-S-4-methoxytrityl-L-cysteine [ No CAS ]
  • C151H256N48O39S [ No CAS ]
YieldReaction ConditionsOperation in experiment
10.2% The titled peptide was synthesized on a model 430A peptide synthesizer (Applied Rio systems, Foster City, Calif., U.S.A.) which was modified to do accelerated Hoc-chemistry solid phase peptide synthesis (Schnolzer, M. et al., mt. J Peptide Protein Res., (1992), 40:180). 4-Methylbenzhydry- lamine (MHHA) resin (Peninsula, Helmont, Calif., U.S.A.), with a substitution of0.91 mmol/g was used. Hoc amino acids (Midwest Hio-Tech, Fishers, Ind., U.S.A.; Novabiochem., San Diego, Calif., U.S.A.) were used with the following side chain protection: Hoc-Ala-OH, Hoc-Arg(Tos)-OH, Hoc-His (DNP)-OH, Hoc-Val-OH, Hoc-Ecu-OH, Hoc-Gly-OH, HocGln-OH, Hoc-Eys(2C1Z)?--OH, Hoc-Ser(Hzl)-OH, Hoc-PheOH, Hoc-Glu(OcHex)-OH and Hoc-Pro-OH. Fmoc-Glu (OtHu)-OH (Novabiochem, San Diego, Calif., U.S.A.) was used for the residue at the 3rd position in the sequence. The synthesis was carried out on a 0.25 mmol scale. The Hoc groups were removed by two treatments with 100percent TFA each lasting one minute. Hoc amino acids (2.5 mmol) were preactivated with HH11J (2.0 mmol) and DIEA (1.0 mE) in 4 mE of DMF and were coupled without prior neutralization of the peptide-resin TFA salt. Coupling times were 5 minutes. At the end of the assembly of the first 25 residues on theAHI 430A® peptide synthesizer and before the coupling of Fmoc-Glu (OtHu)-OH, the protected peptide-resin was transferred into a reaction vessel on a shaker for manual synthesis. After removing the Hoc protecting group with two, one-minute treatments with 100percent TFA and a washing with DMF, the resin was mixed with Fmoc-Glu(OtHu)-OH (2.5 mmol) which was preactivated with HHTU (2.0 mmol), HOHt (2.0 mmol) and DIEA (1.0 mE) in 4 mE of DMF. The mixture was shaken for 2 hours. This coupling step was repeated. After washing with DMF, the resin was treated with a TFA solution containing 5percent water and 5percent TIS for 2 hours to remove the tHu protecting group in the side chain of the Glu residue. The resin was neutralized with 10percent DIEA in DMF and washed with DMF and DCM. The resin was then treated twice with hexylamine (2.0 mmol), DIC (2.0 mmol), HOHt (2.0 mmol) in 5 ml of DCM for two hours per treatment. The resin was washed with DMF and treated with 25percent piperidine in DMF for 30 minutes to remove the Fmoc protecting group. Afier washing with DMF and DCM, the resin was transferred into the reaction vessel on the AHI 430A peptide synthesizer for the assembly of the rest two residues. At the end of the assembly of the whole peptide chain, the resin was treated with a solution of 20percent mercaptoethanol/10percent DIEA in DMF for 2x30 mm to remove the DNP group on the His side chain. The N-terminal Hoc group was then removed by two treatments of 100percent TFA for 2 minutes. The peptide-resin was washed with DMF and DCM and dried under reduced pressure. The final cleavage was done by stirring the peptide-resin in 10 mE of HF containing 1 mE of anisole and dithiothreitol (50 mg) at 0° C. for 75 minutes. HF was removed by a flow of nitrogen. The residue was washed with ether (6x 10 mE) and extracted with 4N HOAc (6x10 mE). This crude product was purified on a reverse-phase preparative HPEC using a colunm (4x43 cm) of C18 DYNAMAX-100A°® (Varian, Walnut Creek, Calif., U.S.A.). The column was eluted with a linear gradient from 75percentAand25percent B to 55percentAand45percent B at flow rate of 10 mE/mm in an hour where A was 0.1percent TFA in water and B was 0.1percent TFA in acetonitrile. Fractions were collected and checked on an analytical HPEC. Those containing pure product were combined and lyophilized to dryness. 31.8 mg of a white solid was obtained. Purity was 89percent based on analytical HPEC analysis. Electro-spray ionization mass spectrometry (ESI MS) analysis gave the molecular weight at 3368.4 (in agreement with the calculated molecular weight of 3368.9).
  • 71
  • Fmoc-Thr(ψ(Me,Me)pro) [ No CAS ]
  • [ 68858-20-8 ]
  • [ 13734-34-4 ]
  • [ 35661-39-3 ]
  • [ 71989-18-9 ]
  • [ 71989-26-9 ]
  • [ 1849-36-1 ]
  • [ 146982-24-3 ]
  • C62H92N10O19S [ No CAS ]
  • 72
  • Fmoc-Thr(ψ(Me,Me)pro) [ No CAS ]
  • [ 29022-11-5 ]
  • [ 13734-34-4 ]
  • [ 35661-39-3 ]
  • [ 1849-36-1 ]
  • [ 146982-24-3 ]
  • C36H46N6O12S [ No CAS ]
  • 73
  • [ 186581-53-3 ]
  • [ 13734-34-4 ]
  • [ 102123-74-0 ]
YieldReaction ConditionsOperation in experiment
1.8 g Vessel A containing KOH (33.6g, 0.6mol) in methanol / H2O (1: 1 by volume) was added, a total of 0.5L; container B containing a methanol solution of diazonium reactant 1-methyl-1-nitrosourea (3.30g, 32mmol) in, 54 mL; Boc vessel C containing protected L- phenylalanine (6.4mmol) and triethylamine (6.72 mmol) in THF 20 mL total; D in container containing ethyl chloroformate (6.4mmol) in THF, a total of 20mL.The reaction vessel C and D in the reaction vessel by tetrafluoroethylene material pumped into the reactor center line II; and the reaction vessels A and B in the reaction vessel was pumped into the pipeline by tetrafluoroethylene I reaction center (where KOH diazo mole ratio of 2: 1), diazomethane generated in the reaction center I reaction centers into the overflow outlet III by reaction center, activated intermediates II reaction center generating a pump into the reaction center of the diazo III the reaction of methane, the reaction product was pumped into the reactor in the center IV; IV simultaneously pumped into the reaction center HCl / THF 2M solution 40mL, 0 after stirring for 10min pumped into the processing center, to give 1.8g of compound A.Yield 95percent, purity HPLC> 98percent.
  • 74
  • [ 3034-22-8 ]
  • [ 13734-34-4 ]
  • C17H20BrN3O3S [ No CAS ]
YieldReaction ConditionsOperation in experiment
General procedure: The relevant Boc-AA1-OH (1.1 equiv), TBTU (1.1 equiv) and DIEA (2.0 equiv) were dissolved in CH2Cl2 anhydrous at room temperature and the mixture stirred for 30 min prior to addition of bromothiazole 5 (1.0 equiv). The mixture was stirred and allowed to proceed at room temperature for further 23h, with periodic monitoring by TLC. The solvent was then reduced at 3mL and the residue was submitted to column chromatography on silica using DCM/Acetone 10:1 (v/v). The product was isolated as oil and identified as the desired product (Boc-3 or Boc-4) by NMR and MS (see also Supporting Information). Boc-3.4: deltaH 10.48 (bs, 1H, -NH-BTZ); 7.28 (s, 1H, -CH2=CH-); 7.19-7.05 (5H, m, -Ar); 4.99 (bs, 1H, -O-CO-NH-); 4.54 (bs, 1H, -NH-CH-); 3.13-3.08 (m, 1H, -CHH-Ph); 3.04-2.99 (m, 1H, -CHH-Ph); 1.33 (s, 9H, -C(CH3)3). deltaC 206.99 (-CO-NH-BTZ); 169.87 (-NH-C=(S)-); 158.16 (-O-CO-); 138.11 (-C1Ph); 135.54 (-CH=CH(Br)-); 129.19 (-C3Ph and ?C5Ph); 128.84 ((-C2Ph and -C6Ph); 127.34 (-C4Ph); 103.78 (-C(CH3)3); 81.08 (-C(Br)=); 68.18 (-CH(-)(CH2-Ph)-); 38.76 (-CH2-Ph); 28.24 (-CH3)3). Yield (77.1percent); ESI-MS calcd for C17H20BrN3O3S [MH+]: 426.04; Found: 426.00. Boc-4: deltaH 7.23-7.21 (m, 2H, Ar); 7.19 (bs, 2 H, -NH-BTZ, -CH(=)-); 7.15-7.10 (m, 2H, Ar); 6.87 (bs, 1H, -CO-NH-CH2-); 5.26 (bs, 1H, -O-CO-NH-); 4.36-4.31 (m, 1H, -NH-CH(-)-); 4.25-4.12 (m, 1H, -NH-CH2-CO-); 4.00-3.95 (m, 1H, -CHH-Ph); 3.93-8.88 (m, 1H, -CHH-Ph); 1.33 (s, 9H, -C(CH3)3). deltaC 172.73 (-CO-NH-CH2-); 169.89 (-CH2-CO-NH-); 167.05 (-C(=N)-); 158.03 (-O-CO-); 138.20 (-CH(=)-); 136.17 (-C1-Ph); 129.19 (-C3-Ph, -C5-Ph); 129.03 (-C2-Ph, -C6-Ph); 128.43 (-C4-Ph); 103.58 (-S-C(Br)=); 85.57 (-C(CH3)3); 68.18 (-CH(-CH2Ph)-); 43.00 (-NH-CH2-CO-); 38.76 (-CH2-Ph); 28.25 (-C(CH3)3). Yield (67.7percent); ESI-MS calcd for C19H24BrN4O4S [MH+]: 482.06; Found: 482.93.
  • 75
  • [ 13734-34-4 ]
  • [ 97-09-6 ]
  • (S)-2-(2-(1-([1,1'-biphenyl]-4-yl)-5-methoxy-2-methyl-1H-indol-3-yl) acetamido)-N-((4-chloro-3-nitrophenyl)sulfonyl)-3-phenylpropanamide [ No CAS ]
  • 76
  • [ 13734-34-4 ]
  • [ 97-09-6 ]
  • (S)-2-amino-N-((4-chloro-3-nitrophenyl)sulfonyl)-3-phenylpropanamide hydrochloride [ No CAS ]
YieldReaction ConditionsOperation in experiment
59% General procedure: (tert-Butoxycarbonyl)-l-phenylalanine (1.3 g, 5 mmol) was dissolved in 30 mL anhydrous THF at 0 C. 5 min later, NMM (0.6 ml, 5.5 mmol) and isobutylchloroformate (0.7 ml, 5.5 mmol) were added successively. After stirred for 1 h, the mixture of benzenesulfonamide (0.86 ml, 5.5 mmol) and NaH (0.5 g, 12.5 mmol), which stirred for 4 h at room temperature, was added and the reaction was warmed slowly to room temperature and stirred overnight. The solvent was removed under low pressure. The resulting residue was extracted with EtOAc and washed with 0.5 M citric acid and brine, respectively. After dried over MgSO4 and concentrated, the obtained oil was dissolved in EtOAc saturated with HCl gas and stirred at room temperature overnight. Then the generated hydrochloride precipitate was filtered and dried.
  • 77
  • [ 13734-34-4 ]
  • [ 169447-86-3 ]
  • 78
  • [ 13734-34-4 ]
  • [ 16652-76-9 ]
  • [ 136282-23-0 ]
YieldReaction ConditionsOperation in experiment
90% With 4-methyl-morpholine; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In tetrahydrofuran; at 0 - 20℃; for 12h;Inert atmosphere; General procedure: A mixture of L-valine p-TsOH salt 10a (100 mg, 0.30 mmol) and N-Boc valine (87.12 mg, 0.30 mmol) was taken in 2.5 mL of dry THF and cooled to 0 C under nitrogen atmosphere. After stirring, freshly distilled NMM (0.16 mL, 1.51 mmol) was added via syringe followed by HOBt (46.61 mg, 0.34mmol) and EDCI (65.18 mg, 0.34 mmol) in a single portion. The mixture was stirred overnight slowly warming to room temperature. After 12 hours, it was concentrated by a rotavapor and the residue was taken in EtOAc (20.0 mL), washed with saturated NaHCO3 solution followed by brine. The organic layer was dried over MgSO4, filtered, and then the solvent was evaporated under reduced pressure. The residue was purified by flash column chromatography using hexane-EtOAc (8:2) to afford the title compound 11a
  • 79
  • [ 112898-00-7 ]
  • [ 13734-34-4 ]
  • C41H50N5O13PolS [ No CAS ]
  • [ 86060-82-4 ]
  • [ 118904-37-3 ]
  • [ 71989-23-6 ]
  • [ 35737-15-6 ]
  • [ 152120-54-2 ]
  • [ 76-05-1 ]
  • C67H104N16O14*2C2HF3O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
4% Six amino acid residues were coupled to the resin-bound peptide (0.2 mmol) synthesized in Example 1 by standard Fmoc based solid phase synthesis. Fmoc deprotections were achieved by two iterative 15-minute treatments of the resin with 20% piperidine in DMF. Couplings were conducted using 3 equivalents of an amino acid derivative, 3 equivalents of DIC, and 3 equivalents HOBt in DMF or NMP (for Fmoc-DGln-OH) with 2-hour reaction times at room temperature. The following amino acid derivatives were used to construct the peptide: Fmoc-Ile-OH, <strong>[118904-37-3]<strong>[118904-37-3]Fmoc-D-allo-Ile</strong>-OH</strong>,Fmoc-D-Gln-OH, Fmoc-Trp-OH, Fmoc-Ile-OH, Boc-D-MePhe-OH. LCMS Analysis - ESI mIz observed: 1647.3, required for [C80H119N13022S + Hf:1646.8.The resin-bound peptide prepared above (pre-swelled in DMF) was treated with K2C03 (55 mg, 0.4 mmol) and 3 x 1 hour cycles of 5% thiophenol in DMF. After each treatment, the resin was filtered and washed with DMF. Removal of the 2-nitrobenzenesulfonyl group was confirmed by a positive Kaiser test. The resin was next treated with a solution of Fmoc-Lys(Cbz)-OH (276 mg, 0.6 mmol) and HBTU (228 mg, 0.6 mmol) in DMF 5 mL. After the reaction was mixed for 1 hour, the resin was filtered and washed with DMF and CH2C12. Complete conversion was confirmed by a negative Kaiser test and LCMS analysis. LCMS analysis - ESI mlz+ observed: 1947.3, required for[C103H144N14023 + H]:1947.1.The resin-bound peptide prepared above was next treated with 20% piperidine in DMF for two 15-minute cycles, after which the resin was washed thoroughly with DMF and CH2C12. The peptide was then cleaved from the resin by 3 x 60 mm treatments with 30% TFE in CH2C12, collecting the filtrate after each treatment. The filtrate wasconcentrated and the desired peptide was isolated by reverse phase flash chromatography (Column: Puriflash 15 tM C18 120 g, Gradient: 40-80% B over 25 minutes at 15 mL/min). Yield- 44.4 mg, 0.024 mmol. LCMS analysis - ESI mlz+ observed: 1723.9, required for [C88H134N14021 + H]:1724.0.A solution of the purified peptide prepared above and NMM (9 tL, 0.09 mmol) inCH2C12 (12 mL) was treated with a solution of 100 mM HATU and 300 mM HOAt inDMF (240 tL). After the reaction was mixed for 1 hour, the solvent was removed in vacuo. Complete conversion to the cyclized peptidolactone was confirmed by LCMS analysis. The crude peptide was used without purification. LCMS analysis - ESI mlz+ observed: 1705.8; required for [C83H134N14020 + H]:1706.0. The crude peptidolactone obtained above was dissolved in MeOH (5 mL) and acetic acid (1 mL). The solution was charged with 10% palladium on carbon (40 mg). The reaction flask was then sealed with a septum and the inner atmosphere was purged with hydrogen gas. After the hydrogenation was allowed to proceed overnight under aslight positive pressure of hydrogen, the reaction was filtered to remove palladium on carbon. Complete removal of the Cbz group was confirmed by LCMS analysis. The solvent was removed in vacuo and the lysine deprotected peptide was purified by reverse phase flash chromatography (column: Puriflash 15 tm, C18, 35g; Gradient: hold at 40% B for 10 minutes, then 40-90% B over 25 minutes at 15 mE/mm). Yield: 22.2 mg, 0.0 132mmol JFA salt). LCMS analysis - ESI mlz+ observed: 1571.9; required for [C80H126N14018 + H]: 1571.9.A solution of the purified peptide obtained above (22.2 mg, 0.0 132 mmol) and iPr 2NEt (6 tL, 0.03 mmol) in CH2C12 was treated with N,N?-Bis-Boc-l -guanylpyrazole (4.9 mg, 0.0 16 mmol) and allowed to react for 24 hours. Complete conversion wasconfirmed by LCMS analysis (ESI mlz+ observed: 1813.9, required for [C91H144N16022 + H] : 1814.1). The solvent was removed in vacuo and the remaining residue was treated with TFA (2 mL). Global deprotection was allowed to proceed for 2 hours, after which the TFA was evaporated. Expulsion of CO2 from the Boc-protectiong group on the typtophan indole nitrogen was slow under acidic conditions at room temperature, so thecrude peptide was dissolved in 50% acetonitrile in water and lyophilized. LCMS analysis of the crude lyophilized solid indicated complete global deprotection. The final product peptide was isolated by reverse phase HPLC (column: Luna 5tm Cl 8, Gradient: 20-40% B over 20 minutes at 40 mL/min). Yield - 12.2 mg, 0.00770 mmol (overall yield from starting resin. LCMS analysis - ESI mlz+ observed: 1357.9, Requiredfor: [C67H104N16014 + H]: 1357.8.Di-TFA salt), 4%
  • 80
  • [ 13734-34-4 ]
  • [ 1147996-34-6 ]
  • C41H50N5O13PolS [ No CAS ]
  • [ 86060-82-4 ]
  • [ 118904-37-3 ]
  • [ 71989-23-6 ]
  • [ 110990-08-4 ]
  • [ 76-05-1 ]
  • C59H101N13O14 [ No CAS ]
YieldReaction ConditionsOperation in experiment
3% Six residues were coupled to the resin-bound peptide (0.2 mmol) synthesized in Example 1 by standard Fmoc based solid phase synthesis. Fmoc deprotections wereachieved by two iterative 15-minute treatments of the resin with 20% piperidine in DMF. Couplings were conducted using 3 equivalents of an amino acid derivative, 3 equivalents of DIC, and 3 equivalents HOBt in DMF or NMP (for Fmoc-D-Gln-OH) with 2-hour reaction times at room temperature. The following amino acid derivatives were used to construct the peptide: Fmoc-Ile-OH, <strong>[118904-37-3]<strong>[118904-37-3]Fmoc-D-allo-Ile</strong>-OH</strong>, Fmoc-D-Lys-OH, Fmoc-IleH Ser(psiMe, Mepro)-OH, Boc-D-MePhe-OH. LCMS Analysis - ESI mlz+ observed:1588.1, required for [C76H122N12022S + H]b:1587.7.The resin-bound peptide obtained above (pre-swelled in DMF) was treated with K2C03 (55 mg, 0.4 mmol) and 3 x 1 hour cycles of 5% thiophenol in DMF. After eachtreatment, the resin was filtered and washed with DMF. Removal of the 2-nitrobenzene sulfonyl group was confirmed by a positive Kaiser test. The resin was next treated with a solution of Fmoc-Lys(Cbz)-OH (276 mg, 0.6 mmol) and HBTU (228 mg, 0.6 mmol) in DMF 5 mL. After the reaction was mixed for 1 hour, the resin was filtered and washed with DMF and CH2C12. Complete conversion was confirmed by a negative Kaiser testand LCMS analysis. LCMS analysis - ESI mlz+ observed: 1888.1, required for [C99H147N13023 + H]:1888.1.The resin-bound peptide obtained above was next treated with 20% piperidine in DMF for two 15-minute cycles, after which the resin was washed thoroughly with DMF and CH2C12. The peptide was then cleaved from the resin by 3 x 60 mm treatments with30% TFE in CH2C12, collecting the filtrate after each treatment. The filtrate was concentrated and the desired peptide was isolated by reverse phase flash chromatography (Column: Puriflash 15 tM C18 120 g, Gradient: 40-80% B over 25 minutes at 15 mL/min). Yield-26.1 mg, 0.0156 mmol. LCMS analysis - ESI mlz+ observed: 1665.1, required for [C84H137N13021 + H]:1665.0.A solution of the purified peptide and i-Pr2NEt (9 jiL, 0.05 mmol) in CH2C12 (7.25 mL) was treated with a solution of 100 mM HBTU DMF (145 tL). After the reaction was mixed for 1 hour, the solvent was removed in vacuo. Complete conversion to the cyclized peptidolactone was confirmed by LCMS analysis. The crude peptidolactone was used without purification. LCMS analysis - ESI mlz+ observed: 1646.8; required for[C84H135N13020 + H]+: 1647.0.The crude peptidolactone obtained above was dissolved in MeOH (2 mL) and acetic acid (200 tL). The solution was charged with 10% palladium on carbon (40 mg). The reaction flask was then sealed with a septum and the inner atmosphere was purged with hydrogen gas. After the hydrogenation was allowed to proceed for 90 minutesunder a slight positive pressure of hydrogen, the reaction mixture was filtered to remove palladium on carbon. Complete removal of the Cbz group was confirmed by LCMS analysis (ESI mlz+ observed: 1512.90; Required for [C76H129N13018 + H]: 1512.97). The filtered peptide solution was concentrated in vacuo and treated with TFA (2 mL) for 1 hour, after which the TFA was evaporated. The final product peptide was isolated byreverse phase HPLC (column: Luna 5tm C18, Gradient: 20-40% B over 20 minutes at 40 mL/min). Yield - 9.7 mg, 0.0062 mmol (tri-TFA salt), 3% overall yield from starting resin. LCMS analysis - ESI mlz+ observed: 1216.8; required for [C59H101N13014 + H]:1216.8.
  • 81
  • [ 13139-16-7 ]
  • [ 13734-34-4 ]
  • [ 16948-16-6 ]
  • [ 82732-07-8 ]
  • [ 66845-42-9 ]
  • C43H56N6O7 [ No CAS ]
  • C86H112N12O14 [ No CAS ]
  • 82
  • [ 13139-16-7 ]
  • [ 13734-34-4 ]
  • [ 16948-16-6 ]
  • [ 82732-07-8 ]
  • [ 66845-42-9 ]
  • C35H50N6O5 [ No CAS ]
  • C70H100N12O10 [ No CAS ]
  • 83
  • [ 13734-34-4 ]
  • [ 22821-76-7 ]
  • [ 154279-16-0 ]
  • 84
  • [ 15761-38-3 ]
  • [ 13734-34-4 ]
  • [ 1376947-86-2 ]
  • [ 2483-46-7 ]
  • [ 1676-90-0 ]
  • [ 13836-37-8 ]
  • C12H24N2O4 [ No CAS ]
  • C16H27N3O6 [ No CAS ]
  • C21H36N4O8 [ No CAS ]
  • C23H34N6O8S [ No CAS ]
  • C19H31N3O8 [ No CAS ]
  • C18H29N3O8 [ No CAS ]
  • Boc-Pro-Phe-Ala-Cys(tBu)-Asp(OtBu)-Ile-Cys(tBu)-Gly-OH [ No CAS ]
  • Boc-Arg(*)-OH [ No CAS ]
  • C137H234N54O34S2 [ No CAS ]
  • 85
  • [ 13734-34-4 ]
  • [ 868540-16-3 ]
Same Skeleton Products
Historical Records

Pharmaceutical Intermediates of
[ 13734-34-4 ]

Bortezomib Related Intermediates

Chemical Structure| 98-97-5

[ 98-97-5 ]

Pyrazine-2-carboxylic acid

Chemical Structure| 196929-78-9

[ 196929-78-9 ]

(R)-2-Methyl-2-propanesulfinamide

Chemical Structure| 73183-34-3

[ 73183-34-3 ]

4,4,4',4',5,5,5',5'-Octamethyl-2,2'-bi(1,3,2-dioxaborolane)

Chemical Structure| 201733-56-4

[ 201733-56-4 ]

5,5,5',5'-Tetramethyl-2,2'-bi(1,3,2-dioxaborinane)

Chemical Structure| 1243174-57-3

[ 1243174-57-3 ]

(R)-3-Methyl-1-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)butan-1-amine hydrochloride

Similar Product of
[ 13734-34-4 ]

Chemical Structure| 84771-22-2

A473077[ 84771-22-2 ]

Boc-L-Phenylalanine-13C

Reason: Stable Isotope

Related Functional Groups of
[ 13734-34-4 ]

Amino Acid Derivatives

Chemical Structure| 128779-47-5

[ 128779-47-5 ]

(R)-3-([1,1'-Biphenyl]-4-yl)-2-((tert-butoxycarbonyl)amino)propanoic acid

Similarity: 0.98

Chemical Structure| 76932-48-4

[ 76932-48-4 ]

(R)-2-((tert-Butoxycarbonyl)amino)-3-(naphthalen-1-yl)propanoic acid

Similarity: 0.97

Chemical Structure| 76985-10-9

[ 76985-10-9 ]

Boc-D-2-Nal-OH

Similarity: 0.97

Chemical Structure| 58438-04-3

[ 58438-04-3 ]

Boc-2-Nal-OH

Similarity: 0.97

Chemical Structure| 51987-73-6

[ 51987-73-6 ]

Methyl (tert-butoxycarbonyl)-L-phenylalaninate

Similarity: 0.95