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Chemical Structure| 15761-39-4 Chemical Structure| 15761-39-4
Chemical Structure| 15761-39-4

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Boc-Pro-OH is a biochemical reagent, used as a biomaterial or organic compound for life science-related research.

Synonyms: NSC 164660; 1-tert-butyloxycarbonyl-L-Proline; N-Boc-L-Proline

4.5 *For Research Use Only !

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Product Citations

Product Citations

Canale, Vittorio ; Kaminski, Michal ; Trybala, Wojciech ; Abram, Michal ; Marciniec, Krzysztof ; Bantreil, Xavier , et al.

Abstract: A solid-state approach was used to synthesize compound PZ-1190, a multitarget ligand for serotonin and dopamine receptors with potential antipsychotic activity in rodents. Compared to the classical batch synthesis approach, the developed multistep mechanochem. protocol improved the overall yield (from 32% to 56%), reduced the reaction time (from 42 to 4 h), and decreased the use of toxic reagents and organic solvents. All synthesized intermediates and PZ-1190 were isolated in high purity by extraction without the requirement of chromatog. purification PZ-1190 was obtained in high enantiomeric purity (≥99% ee) with no impact of grinding processes on the integrity of stereocenter. The described procedures represent rare examples of mechanochem. reduction of a carboxylic function, which might open up the possibility to obtain crucial β- and γ-amino alcs. in a sustainable manner. The oxidation of an aliphatic alc. into an aldehyde using mechanochem. has also been reported for the first time. The obtained results confirmed the suitability of mechanochem. as a sustainable and efficient method of synthesizing candidates for preclin. development.

Keywords: Azinesulfonamide derivatives ; Multistep mechanochemicalsynthesis ; Medicinal mechanochemistry ; Green chemistry ; Antipsychotic agents

Alternative Products

Product Details of Boc-Pro-OH

CAS No. :15761-39-4
Formula : C10H17NO4
M.W : 215.25
SMILES Code : O=C(O)[C@H]1N(C(OC(C)(C)C)=O)CCC1
Synonyms :
NSC 164660; 1-tert-butyloxycarbonyl-L-Proline; N-Boc-L-Proline
MDL No. :MFCD00037324
InChI Key :ZQEBQGAAWMOMAI-ZETCQYMHSA-N
Pubchem ID :85083

Safety of Boc-Pro-OH

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

Application In Synthesis of Boc-Pro-OH

* 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 [ 15761-39-4 ]

[ 15761-39-4 ] Synthesis Path-Downstream   1~35

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  • 3
  • [ 15761-39-4 ]
  • [ 13734-34-4 ]
  • [ 40350-83-2 ]
  • Boc-L-Arg(Tos)-OH [ No CAS ]
  • Boc-Ser(OBzl), Boc-Leu, Boc-Cys(Meb), Boc-Gly [ No CAS ]
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  • 4
  • [ 15761-39-4 ]
  • [ 13734-34-4 ]
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  • Boc-D-Arg(Tos)-OH [ No CAS ]
  • Boc-Ser(OBzl), Boc-Cys(Meb), Boc-Gly, Boc-Leu [ No CAS ]
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  • 5
  • [ 4530-20-5 ]
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  • [ 40350-83-2 ]
  • Boc-L-Arg(Tos)-OH [ No CAS ]
  • Boc-Phe, Boc-Ser(OBzl), Boc-Leu, Boc-Cys(Meb) [ No CAS ]
  • [ 140661-81-0 ]
  • 6
  • [ 15761-39-4 ]
  • [ 13734-34-4 ]
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  • Boc-L-Arg(Tos)-OH [ No CAS ]
  • Boc-Ser(OBzl), Boc-Cys(Meb), Boc-Gly [ No CAS ]
  • [ 140661-89-8 ]
  • 7
  • [ 15761-39-4 ]
  • [ 40350-83-2 ]
  • Boc-L-Arg(Tos)-OH [ No CAS ]
  • Boc-D-Arg(Tos)-OH [ No CAS ]
  • Boc-Gly, Boc-Phe, Boc-Ser(OBzl), Boc-Leu, Boc-D-Phe [ No CAS ]
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  • 8
  • [ 4530-20-5 ]
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  • [ 40350-83-2 ]
  • Boc-Phe-OH, Boc-Ser(OBzl)-OH, Boc-D-Phe-OH, Boc-Leu-OH, Boc-D-Arg(Tos)-OH [ No CAS ]
  • [ 135701-67-6 ]
  • 9
  • [ 15761-39-4 ]
  • [ 13734-34-4 ]
  • [ 40350-83-2 ]
  • Boc-L-Arg(Tos)-OH [ No CAS ]
  • Boc-Leu, Boc-Cys(Meb), Boc-Gly [ No CAS ]
  • [ 140661-86-5 ]
  • 10
  • [ 15761-39-4 ]
  • [ 40350-83-2 ]
  • Boc-L-Arg(Tos)-OH [ No CAS ]
  • Boc-D-Arg(Tos)-OH [ No CAS ]
  • Boc-Ser(OBzl), Boc-Cys(Meb), Boc-Gly, Boc-D-Phe, Boc-Phe [ No CAS ]
  • [ 109333-26-8 ]
  • 11
  • [ 4530-20-5 ]
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  • [ 40350-83-2 ]
  • Boc-L-Arg(Tos)-OH [ No CAS ]
  • Boc-Phe, Boc-Ser(OBzl), Boc-Leu, Boc-D-Cys(Meb) [ No CAS ]
  • [ 140661-79-6 ]
  • 12
  • [ 4530-20-5 ]
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  • [ 40350-83-2 ]
  • Boc-L-Arg(Tos)-OH [ No CAS ]
  • Boc-Phe, Boc-Ser(OBzl), Boc-Leu, Boc-Cys(Meb) [ No CAS ]
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  • 13
  • [ 15761-39-4 ]
  • [ 13734-34-4 ]
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  • Boc-L-Arg(Tos)-OH [ No CAS ]
  • Boc-Ser(OBzl), Boc-Leu, Boc-D-Cys(Meb), Boc-Gly [ No CAS ]
  • [ 140661-87-6 ]
  • 14
  • [ 15761-39-4 ]
  • [ 13734-34-4 ]
  • [ 40350-83-2 ]
  • Boc-L-Arg(Tos)-OH [ No CAS ]
  • Boc-Ser(OBzl), Boc-Leu, Boc-Cys(Meb), Boc-Gly [ No CAS ]
  • [ 140661-87-6 ]
  • 15
  • [ 15761-39-4 ]
  • [ 13734-34-4 ]
  • [ 40350-83-2 ]
  • Boc-L-Arg(Tos)-OH [ No CAS ]
  • Boc-Ser(OBzl), Boc-Leu, Boc-D-Cys(Meb) [ No CAS ]
  • [ 140661-83-2 ]
  • 16
  • [ 15761-39-4 ]
  • [ 13734-34-4 ]
  • [ 40350-83-2 ]
  • Boc-L-Arg(Tos)-OH [ No CAS ]
  • Boc-Ser(OBzl), Boc-Leu, Boc-Cys(Meb) [ No CAS ]
  • [ 140661-83-2 ]
  • 17
  • [ 15761-39-4 ]
  • [ 22259-53-6 ]
  • 2-[(1<i>H</i>-indol-3-ylmethyl)-carbamoyl]-pyrrolidine-1-carboxylic acid <i>tert</i>-butyl ester [ No CAS ]
  • 18
  • [ 15761-39-4 ]
  • Boc-MePhe-N(-CH2-Merrifield resin)-Phe-OMeBoc-Leu-OH [ No CAS ]
  • [ 38136-70-8 ]
  • 19
  • [ 15761-39-4 ]
  • Boc-MePhe-N(-CH2-Merrifield resin)-Phe-OMeBoc-Leu-OH [ No CAS ]
  • [ 142253-50-7 ]
  • 20
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  • [ 16947-63-0 ]
  • C18H25N3O5 [ No CAS ]
  • 21
  • [ 15761-39-4 ]
  • [ 3321-03-7 ]
  • [ 76-05-1 ]
  • C2HF3O2*C16H21N3O4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Peptide analogs of RPPGF (Arg-Pro-Pro-<strong>[3321-03-7]Gly-Phe</strong>, SEQ ID NO:4) were prepared by traditional solid-phase peptide synthesis (Merrifield R B. J. Amer. Chem. Soc. 85, 2149-2154 (1963)) in conjunction with the ?tea-bag? methodology (Houghten R A. Proc. Natl. Acad. Sci. 82, 5131-5135 (1985)) using Boc/benzyl based chemistry. The peptides were assembled on Methylbenzhydrylamine resin (MBHA resin) using traditional Boc/Benzyl based chemistry. The protected amino acids were Boc-Arg (Tos), Boc-D-Arg (Tos), Boc-Gly, Boc-Phe, Boc-Pro, Boc-F5F, Boc-Hyp, Boc-Idg, Boc-Oic, Boc-Tic, and Boc-Thi with Boc being tert-butyloxycarbonyl, F5F being Pentafluorophenylanine, Hyp being L-4-Hydroxyproline, Idg being alpha-(2-indanyl)glycine, Oic being Octhydroindole-2-carboxylic acid, Tic being Tetrahydroisoquinoline-3-carboxylic acid, Thi being beta-(20Thienyl)-alanine, and Tos being Tosyl. In order to begin the synthesis, bags made of a polypropylene mesh material are filled with resin. The bags are then placed in a Nalgene bottle with dichloromethane (DCM) and shaken 5 min to allow the swelling of the resin. The DCM solution is then discarded and the actual synthesis is performed. The resin packets were washed 3 times, 2 minutes each time, with 5% diisopropylethylamine (DIEA) in DCM (neutralization step) then with DCM (2×1 min) to remove excess base. After neutralization, the packets are sorted and placed in Nalgene bottles containing the amino acid of interest in DCM. An equal amount of activator [diisopropylcarbodiimide (DIC)] in DCM is added and the coupling reaction is started. After shaking for 1 h, the packets are washed twice with DMF followed by a final two washes with DCM. The N-alpha-t-Boc is removed by acidolysis using 55% trifluoroacetonitril (TFA) in DCM for 30 min, leaving a TFA salt of the alpha-amino group. The bags are then washed successively with DCM (1×1 min), isopropanol (2×1 min) and DCM (1×1 min) to remove any residual TFA. This procedure is repeated for the addition of each amino acid at the coupling step. After completion of the synthesis and final tert-butyloxycarbonyl (Boc) removal, the peptides are side chain deprotected and cleaved from the resin at 0 C. with liquid hydrogen fluoride (HF) in the presence of anisole as a carbocation scavenger. The procedure is performed in a 10-vessel HF apparatus (Houghten et al. Int. J. Peptide Res. 27, 673-678 (1985)). The reaction is allowed to proceed for 60 min. Liquid HF is then removed using a strong flow of N2 for 90 min followed by the use of aspirator vacuum for 60 min while maintaining the temperature at 0 C. The reaction vessels were disconnected from the apparatus and the residual anisole was removed from the resin with two ethylether washes. The peptides are then extracted with 10% acetic hydroxide washes and the extraction solutions are pooled and lyophilized. The crude peptides are weighed and stored under nitrogen and subsequently analyzed by analytical RP-HPLC and by mass spectral analysis.
  • 22
  • boc-Gly-Merrifield resin [ No CAS ]
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  • [ 13734-41-3 ]
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  • [ 81-88-9 ]
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  • 24
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  • [ 55984-93-5 ]
  • [ 1588517-23-0 ]
  • [ 1588517-24-1 ]
  • 25
  • [ 82104-74-3 ]
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  • [ 1588517-25-2 ]
  • 26
  • polyethylene glycol polyamide resin [ No CAS ]
  • [ 15761-39-4 ]
  • [ 23680-31-1 ]
  • [ 61925-77-7 ]
  • [ 47689-67-8 ]
  • [ 170384-29-9 ]
  • C60H69BrN7O13PolS [ No CAS ]
  • 27
  • [ 15761-39-4 ]
  • [ 84-67-3 ]
  • (2S,2'S)-di-tert-butyl 2,2'-(((2,2'-dimethyl-[1,1'-biphenyl]-4,4'-diyl)bis(azanediyl))bis(carbonyl))bis(pyrrolidine-1-carboxylate) [ No CAS ]
YieldReaction ConditionsOperation in experiment
96% With N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; In dichloromethane; at 20℃; for 2h; General procedure: 5.1.1.14. (2S,2'S)-Di-tert-butyl 2,2'-(((3,3'-dimethyl-[1,1'-biphenyl]-4,4'-diyl)bis(azanediyl))bis(carbonyl))bis(pyrrolidine-1-carboxylate) (17). A mixture of N-Boc-L-proline (9.47 g, 44.0 mmol), EDCI(9.97 g, 52.0 mmol), and ortho-tolidine (4.25 g, 20.0 mmol) inCH2Cl2 (30 mL) was stirred at ambient temperature for 2 h. Theresulting residue was partitioned between CH2Cl2 and H2O. Theorganic layer was washed with 1.0 N aq HCl solution and brine,dried over MgSO4, filtered, and concentrated in vacuo. Without anypurification, 3 was obtained as a solid (11.3 g, 93percent).; 5.1.1.16 (2S,2'S)-Di-tert-butyl 2,2'-(((2,2'-dimethyl-[1,1'-biphenyl]-4,4'-diyl)bis(azanediyl))bis(carbonyl))bis(pyrrolidine-1-carboxylate) (19) Yield 2.75 g (96percent). 1H NMR (DMSO-d6, delta = 2.5 ppm, 400 MHz): 9.97 (s, 2H), 7.57-7.41 (m, 4H), 6.97 (app br s, 2H), 4.26 (m, 2H), 3.42-3.35 (m, 4H), 2.21 (m, 2H), 1.97 (s, 6H), 1.89-1.78 (m, 6H), 1.40-1.31 (app br s, 18H). 13C NMR (DMSO-d6, delta = 39.52 ppm, 100 MHz): 171.4, 171.0, 153.6, 153.2, 138.0, 138.0, 135.69, 135.65, 129.52, 120.48, 120.47, 120.4, 120.3, 116.7, 116.5, 78.6, 78.4, 60.3, 60.0, 46.7, 46.5, 31.3, 31.1, 30.2, 28.1, 28.0, 23.9, 23.3, 19.7. HRMS: Anal. calcd. for [M+H]+ C34H46N4O6: 607.3490; found 607.3489.
96% With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; at 20℃; for 2h; Example 3 Preparation of dimethyl((1R,1'R)-((2S,2'S)-2,2'-(((2,2'-dimethyl-[1,1'-biphenyl]-4,4'-diyl)bis(azandiyl))bis(carbonyl))bis(pyrrolidine-2,1-diyl))bis(2-oxo-1-phenylethane-2,1-diyl))dicarbamate N-Boc-L-proline (2.23 g, 10.4 mmol), EDC (2.35 g, 12.3 mmol), and <strong>[84-67-3]meta-tolidine</strong> (1.0 g, 4.7 mmol) were mixed in CH2Cl2 (10 mL), followed by stirring at room temperature for 2 hours. Then, the compound obtained above was fractionated with CH2Cl2 and H2O. The organic layer was washed with 1 N HCl aqueous solution and brine, dried over MgSO4, filtered, and concentrated under reduced pressure. Without any additional purification process, (2S,2'S)-di-tert-butyl 2,2'-(((2,2'-dimethyl-[1,1'-biphenyl]-4,4'-diyl)bis(azandiyl))bis(carbonyl))bis(pyrrolidine-1-carboxylate), the target compound, was obtained as a solid (2.75 g, yield: 96percent).
  • 28
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  • [ 84-67-3 ]
  • dimethyl((1R,1'R)-((2S,2'S)-2,2'-(((2,2'-dimethyl-[1,1'-biphenyl]-4,4'-diyl)bis(azandiyl))bis(carbonyl))bis(pyrrolidine-2,1-diyl))bis(2-oxo-1-phenylethane-2,1-diyl))dicarbamate [ No CAS ]
  • 29
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  • [ 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).
  • 30
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  • [ 745017-94-1 ]
  • 31
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  • [ 33209-01-7 ]
  • (S)-2-(((2S,3R)-1-amino-3-hydroxy-1-oxobutane-2-yl)carbamoyl)pyrrolidine-1-formic acid tert-butyl [ No CAS ]
YieldReaction ConditionsOperation in experiment
36.2% The N-tert-butoxycarbonyl-L-proline 1e (2.15 g, 10 mmol, using known method "Organic Letters, 2014, 16 (2), 432 - 435" prepared by the) dissolved in 50 ml dichloromethane in, adding 1-(3-dimethylaminopropyl)-3-ethyl carbodiimide (2.3 g, 12 mmol), 1-hydroxy benzotriazole (1.62 g, 12 mmol) and N-methyl morpholine (3.3 ml, 30 mmol), stirring reaction for 1 hour, adding <strong>[33209-01-7]L-<strong>[33209-01-7]threonine amide hydrochloride</strong></strong> (1.55 g, 10 mmol, the Patent application "WO20050182262" disclosed method prepared), stirring for 16 hours. The reaction solution is added in 200 ml dichloromethane, for 1 M salt is washed with an acid (50 ml), anhydrous sodium sulfate drying, filtering, the filtrate is concentrated, with silica gel column chromatography using eluent system A purifying the obtained residue, to obtain the title compound 1 f (1.14 g, white foam solid), yield: 36.2percent.
  • 32
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  • [ 142253-50-7 ]
  • 33
  • [ 15761-39-4 ]
  • [ 430-67-1 ]
  • [ 5680-79-5 ]
  • [ 108-24-7 ]
  • [ 40350-83-2 ]
  • Ac-Pro-Hyp-Gly-OCH<SUB>2</SUB>CHF<SUB>2</SUB> [ No CAS ]
  • 34
  • [ 22300-52-3 ]
  • [ 15761-39-4 ]
  • tert-butyl 2-(4,5-dibromo-2H-1,2,3-triazol-2-yl)pyrrolidine-1-carboxylate [ No CAS ]
  • 35
  • [ 15761-39-4 ]
  • [ 6294-52-6 ]
  • (S)-tert-butyl 2-((5,6-dimethoxybenzo[d]thiazol-2-yl)carbamoyl)pyrrolidine-1-carboxylate [ No CAS ]
 

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