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Cas Database

15761-39-4

15761-39-4

Identification

  • Product Name:1,2-Pyrrolidinedicarboxylicacid, 1-(1,1-dimethylethyl) ester, (2S)-

  • CAS Number: 15761-39-4

  • EINECS:239-848-3

  • Molecular Weight:215.249

  • Molecular Formula: C10H17NO4

  • HS Code:2933 99 80

  • Mol File:15761-39-4.mol

Synonyms:Boc-Pro-OH;(2S)-1,2-Pyrrolidinedicarboxylic acid1-(1,1-dimethylethyl) ester;(S)-1-(tert-Butoxycarbonyl)-2-pyrrolidinecarboxylicacid;1-(tert-Butoxycarbonyl)-(S)-proline;1-tert-Butyloxycarbonyl-L-proline;L-N-Boc-proline;N-(tert-Butoxycarbonyl)-L-proline;N-(tert-Butyloxycarbonyl)-L-proline;N-[(1,1-Dimethylethoxy)carbonyl]-(S)-proline;Boc-L-Proline;

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Safety information and MSDS view more

  • Pictogram(s):HarmfulXn

  • Hazard Codes:Xn

  • Signal Word:No signal word.

  • Hazard Statement:none

  • First-aid measures: General adviceConsult a physician. Show this safety data sheet to the doctor in attendance.If inhaled If breathed in, move person into fresh air. If not breathing, give artificial respiration. Consult a physician. In case of skin contact Wash off with soap and plenty of water. Consult a physician. In case of eye contact Rinse thoroughly with plenty of water for at least 15 minutes and consult a physician. If swallowed Never give anything by mouth to an unconscious person. Rinse mouth with water. Consult a physician.

  • Fire-fighting measures: Suitable extinguishing media Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide. Wear self-contained breathing apparatus for firefighting if necessary.

  • Accidental release measures: Use personal protective equipment. Avoid dust formation. Avoid breathing vapours, mist or gas. Ensure adequate ventilation. Evacuate personnel to safe areas. Avoid breathing dust. For personal protection see section 8. Prevent further leakage or spillage if safe to do so. Do not let product enter drains. Discharge into the environment must be avoided. Pick up and arrange disposal. Sweep up and shovel. Keep in suitable, closed containers for disposal.

  • Handling and storage: Avoid contact with skin and eyes. Avoid formation of dust and aerosols. Avoid exposure - obtain special instructions before use.Provide appropriate exhaust ventilation at places where dust is formed. For precautions see section 2.2. Store in cool place. Keep container tightly closed in a dry and well-ventilated place.

  • Exposure controls/personal protection:Occupational Exposure limit valuesBiological limit values Handle in accordance with good industrial hygiene and safety practice. Wash hands before breaks and at the end of workday. Eye/face protection Safety glasses with side-shields conforming to EN166. Use equipment for eye protection tested and approved under appropriate government standards such as NIOSH (US) or EN 166(EU). Skin protection Wear impervious clothing. The type of protective equipment must be selected according to the concentration and amount of the dangerous substance at the specific workplace. Handle with gloves. Gloves must be inspected prior to use. Use proper glove removal technique(without touching glove's outer surface) to avoid skin contact with this product. Dispose of contaminated gloves after use in accordance with applicable laws and good laboratory practices. Wash and dry hands. The selected protective gloves have to satisfy the specifications of EU Directive 89/686/EEC and the standard EN 374 derived from it. Respiratory protection Wear dust mask when handling large quantities. Thermal hazards

Supplier and reference price

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  • Manufacture/Brand:TRC
  • Product Description:N-Boc-L-proline
  • Packaging:50 g
  • Price:$ 120
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  • Manufacture/Brand:TCI Chemical
  • Product Description:N-(tert-Butoxycarbonyl)-L-proline >99.0%(T)
  • Packaging:25g
  • Price:$ 68
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  • Manufacture/Brand:TCI Chemical
  • Product Description:N-(tert-Butoxycarbonyl)-L-proline >99.0%(T)
  • Packaging:5g
  • Price:$ 23
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  • Manufacture/Brand:SynQuest Laboratories
  • Product Description:(2S)-Pyrrolidine-2-carboxylic acid, N-Boc protected
  • Packaging:5 g
  • Price:$ 20
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  • Manufacture/Brand:Sigma-Aldrich
  • Product Description:Boc-Pro-OH ≥99.0% (T)
  • Packaging:100g
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  • Manufacture/Brand:Sigma-Aldrich
  • Product Description:Boc-Pro-OH Novabiochem . CAS 15761-39-4, molar mass 215.25 g/mol., Novabiochem
  • Packaging:8530030100
  • Price:$ 98.5
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  • Manufacture/Brand:Sigma-Aldrich
  • Product Description:Boc-Pro-OH Novabiochem?
  • Packaging:100 g
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  • Manufacture/Brand:Sigma-Aldrich
  • Product Description:Boc-Pro-OH 99%
  • Packaging:25g
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  • Manufacture/Brand:Sigma-Aldrich
  • Product Description:Boc-Pro-OH ≥99.0% (T)
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  • Manufacture/Brand:Sigma-Aldrich
  • Product Description:Boc-Pro-OH Novabiochem?
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Relevant articles and documentsAll total 183 Articles be found

Design, Synthesis, and Biological Evaluations of Several Y-26732 Analogues

Wang, Xinran,Chen, Ligong,Li, Hang,Sun, Changhai,Qi, Haofei,Wang, Donghua

, p. 1212 - 1218 (2015)

A series of pyridine Rho kinase inhibitors were designed and synthesized utilizing the ligand-binding pocket model with Y-26732 as the lead compound. These compounds were evaluated on cell lines for their biological activities.

-

Bayer,E. et al.

, p. 4853 - 4860 (1968)

-

Direct evidence of significantly different chemical behavior and excited-state dynamics of 1,7- and 1,6-regioisomers of pyrrolidinyl-substituted perylene diimide

Dubey, Rajeev K.,Niemi, Marja,Kaunisto, Kimmo,Efimov, Alexander,Tkachenko, Nikolai V.,Lemmetyinen, Helge

, p. 6791 - 6806 (2013)

Novel bay-functionalized perylene diimides with additional substitution sites close to the perylene core have been prepared by the reaction between 1,7(6)-dibromoperylene diimide 6 (dibromo-PDI) and 2-(benzyloxymethyl) pyrrolidine 5. Distinct differences in the chemical behaviors of the 1,7- and 1,6-regioisomers have been discerned. While the 1,6-dibromo-PDI produced the corresponding 1,6-bis-substituted derivative more efficiently, the 1,7-dibromo-PDI underwent predominant mono-debromination, yielding a mono-substituted PDI along with a small amount of the corresponding 1,7-bis-substituted compound. By varying the reaction conditions, a controlled stepwise bis-substitution of the bromo substituents was also achieved, allowing the direct synthesis of asymmetrical 1,6- and 1,7-PDIs. The compounds were isolated as individual regioisomers. Fullerene (C60) was then covalently linked at the bay region of the newly prepared PDIs. In this way, two separate sets of perylene diimide-fullerene dyads, namely single-bridged (SB-1,7-PDI-C60 and SB-1,6-PDI-C60) and double-bridged (DB-1,7-PDI-C60 and DB-1,6-PDI-C60), were synthesized. The fullerene was intentionally attached at the bay region of the PDI to achieve close proximity of the two chromophores and to ensure an efficient photoinduced electron transfer. A detailed study of the photodynamics has revealed that photoinduced electron transfer from the perylene diimide chromophore to the fullerene occurs in all four dyads in polar benzonitrile, and also occurs in the single-bridged dyads in nonpolar toluene. The process was found to be substantially faster and more efficient in the dyads containing the 1,7-regioisomer, both for the singly- and double-bridged molecules. In the case of the single-bridged dyads, SB-1,7-PDI-C60 and SB-1,6-PDI-C60, different relaxation pathways of their charge-separated states have been discovered. To the best of our knowledge, this is the first observation of photoinduced electron transfer in PDI-C60 dyads in a nonpolar medium. Copyright

Design, synthesis and evaluation of novel 2-hydroxypyrrolobenzodiazepine-5, 11-dione analogues as potent angiotensin converting enzyme (ACE) inhibitors

Sun, Ying,Bai, Yujun,He, Xirui,Bai, Yajun,Liu, Pei,Zhao, Zefeng,Chen, Xufei,Zheng, Xiaohui

, (2017)

Under the guidance of combination of traditional Chinese medicine chemistry (CTCMC), this study describes the preparation of a phenolic acid/dipeptide/borneol hybrid consisting of phenolic acid and a bornyl moiety connected to the dipeptide N-terminal and C-terminal respectively. It also evaluates their angiotensin converting enzyme (ACE) inhibitory and synergistic antihypertensive activities. Briefly, a series of novel 2-hydroxypyrrolobenzodiazepine-5, 11-dione analogues were prepared and investigated for their ability to inhibit ACE. The influence of the phenolic acid and bornyl moiety on subsite selectivity is also demonstrated. Among all the new compounds, two compounds-7a and 7g-reveal good inhibition potency in in vitro ACE-inhibitory tests. Interestingly, favorable binding results in molecular docking studies also supported the in vitro results. Additionally, the bioassay showed that oral administration of the two compounds displayed high and long-lasting antihypertensive activity both in acute antihypertensive tests and in therapeutic antihypertensive tests by non-invasive blood pressure measurements in spontaneously hypertensive rats.

Contiguous generation of quaternary and tertiary stereocenters: One-pot synthesis of chroman-fused S-proline-derived chiral oxazepinones

Singh, Ritesh,Parai, Maloy Kumar,Mondal, Sankalan,Panda, Gautam

, p. 253 - 259 (2013)

A new class of chroman-fused S-proline-derived chiral oxazepinones has been synthesized in one pot through contiguous generation of quaternary and tertiary stereocenters.

Intramolecular Alkylation of Carboxylic Acids: Application to the Synthesis of Boc-Protected Cyclic Amino Acids

Nicola, A. De,Einhorn, C.,Einhorn, J.,Luche, J. L.

, p. 879 - 880 (1994)

A new synthesis of Boc-protected cyclic amino acids is described as an application of an unreported method of lithium diisopropylamide-induced cyclisation of ω-chloro carboxylic acids containing a protected amine function in the chain.

Synthesis of alexine-like compounds from chiral five-membered endocyclic enecarbamates

Valle, Marcelo Siqueira,Retailleau, Pascal,Correia, Carlos Roque Duarte

, p. 1957 - 1960 (2008)

Stereoselective syntheses of enantiomerically enriched trihydroxy pyrrolizidine and indolizidines were accomplished from a common chiral endocyclic enecarbamate. The synthetic strategy features an efficient [2+2] cycloaddition of ketenes to the endocyclic enecarbamate and a highly regioselective Baeyer-Villiger oxidation of the intermediate azabicyclic-cyclobutanones. These new heterocycles are compounds structurally related to the alexines.

Hydrolysis of Pro-Ala Dipeptides by Lysosomal Hydrolases. Models for the Study of Lysosomotropic Amino Acid Prodrugs of Penicillins

Renard, C,Michel, A.,Tulkens, P. M.

, p. 1291 - 1293 (1986)

Peptidic lysosomotropic prodrugs of antibiotics and antitumoral agents could be of advantage in chemotherapy, providing that free, active drug is released at, or close to, the desired site of action.Thus, aminoacyl derivatives of doxorubicin, e.g., where the drug is attached to the amino acid by a primary amino function, are sensitive to lysosomal hydrolases.We have examined whether a similar approach can be used for drugs carrying a carboxyl group such as β-lactam antibiotics.Because the C adjacent to the carboxyl group in β-lactams has the D configuration, we have examined and report here the synthesis and susceptibility of model peptides, namely Boc-D-Pro-L-Ala and Boc-L-Pro-L-Ala to lysosomal hydrolases.Hydrolysis of the D isomer proceeds considerably more slowly than that of the L isomer.Lysosomal carboxypeptidase(s) and/or amidases appear therefore to have a much narrower specificity than aminopeptidase(s), which will severely limit the applicability of the concept of peptidic lysosomotropic prodrugs.

Synthesis and biological evaluation of pyrrolidine-2-carbonitrile and 4-fluoropyrrolidine-2-carbonitrile derivatives as dipeptidyl peptidase-4 inhibitors for the treatment of type 2 diabetes

Wang, Jiang,Feng, Ying,Ji, Xun,Deng, Guanghui,Leng, Ying,Liu, Hong

, p. 7418 - 7429 (2013)

A novel series of pyrrolidine-2-carbonitrile and 4-fluoropyrrolidine-2- carbonitrile derivatives was designed, synthesized, and found to act as dipeptidyl peptidase-4 (DPP-4) inhibitors. From this series of compounds, compound 17a was identified as an efficacious, safe, and selective inhibitor of DPP-4. In vivo studies in ICR and KKAy mice showed that administration of this compound resulted in decreased blood glucose in these mice after an oral glucose challenge. Compound 17a showed high DPP-4 inhibitory activity (IC50 = 0.017 μM), moderate selectivity against DPP-4 (selective ratio: DPP-8/DPP-4 = 1324; DPP-9/DPP-4 = 1164), and good efficacy in oral glucose tolerance tests in ICR and KKAy mice. These in vivo anti-diabetic properties and its desirable pharmacokinetic profile in Sprague-Dawley rats demonstrate that compound 17a is a promising candidate for development as an anti-diabetic agent.

Enantioselective synthesis of (R)-homoboroproline from (S)-proline using a borylation approach

Georgiou, Irene,Whiting, Andrew

, p. 4110 - 4113 (2012)

(S)-Proline was converted through a five-step sequence into (R)-homoboroproline hydrochloride in 29% overall yield with 97% The key step was the conversion of N-Boc iodomethylpyrrolidine into the corresponding pinacol boronate ester by an efficient copper(I)-catalyzed borylation reaction by using bispinacolatodiboron.

Formal Fluorinative Ring Opening of 2-Benzoylpyrrolidines Utilizing [1,2]-Phospha-Brook Rearrangement for Synthesis of 2-Aryl-3-fluoropiperidines

Kondoh, Azusa,Ojima, Rihaku,Terada, Masahiro

supporting information, p. 7894 - 7899 (2021/10/20)

A ring expansion of 2-benzoylpyrrolidines, which involves the formal fluorinative ring opening utilizing the [1,2]-phospha-Brook rearrangement under Br?nsted base catalysis and a subsequent intramolecular reductive amination, was developed. The operationally simple three-step protocol provides an efficient access to 2-aryl-3-fluoropiperidines. The methodology was further applied to the syntheses of azepanes and tetrahydroquinolines.

Recyclable Helical Poly(phenyl isocyanide)-Supported l-Proline Catalyst for Direct Asymmetric Aldol Reaction in Brine

Li, Chonglong,Wang, Jihai,Ding, Huiyun

, p. 1180 - 1190 (2020/09/07)

Abstract: A novel helical poly(phenyl isocyanide) bearing Boc protected l-proline pendants (poly-1m) was designed and synthesized. Removed the protecting Boc groups on the l-proline pendants led to the formation of helical polymer poly-2m, which showed high optical activity owing to the preferred right-handed helix of polyisocyanide main chain. Optically active helical poly-2m showed excellent catalytic ability on asymmetric aldol reaction. Helical polymer catalysts exhibited enhanced stereoselectivity in aldol reaction compared to small molecule l-proline. Under the optimized aldol reaction condition, the enantiomeric excess (ee) and diastereomeric ratio (dr) values of the aldol reaction product were respectively up to 90% and > 20/1. Moreover, the helical polyisocyanide catalyst Poly-2m can be easily recovered and reused in the aldol reaction for at least five cycles with maintained its activity and stereoselectivity. Graphic Abstract: Enantioselective aldol reaction catalyzed by poly-2m.[Figure not available: see fulltext.]

Leonurine derivative and application thereof in preparing medicine for preventing or treating ischemic cerebrovascular diseases

-

Paragraph 0110-0112, (2021/03/30)

The invention provides a leonurine derivative and application of the leonurine derivative in preparation of a medicine for preventing or treating ischemic cerebrovascular diseases. The leonurine derivative has a structure as shown in a general formula (I), wherein X is selected from O or NH; Y is selected from any one of natural amino acid, substituted amino acid or amino alcohol; Z is selected from H, proline and any substituted proline. Pharmacological experiments prove that the leonurine derivative provided by the invention has the effects of neuroprotection, cerebral infarction area reduction and animal neurobehavioral scoring, and is good in safety, so that the leonurine derivative has important significance for developing novel medicines for preventing or treating ischemic cerebrovascular diseases.

A Bifunctional B,N-Based Asymmetric Catalytic Nitrostyrene-Michael Addition Acting through a 10-Membered Ring Cyclic Transition State

Du, Yihao,Erdem, Safiye S.,Sari, Ozlem,Whiting, Andrew

, (2021/11/17)

The B,N-bifunctional catalyst homoboroproline has been applied to a catalytic asymmetric nitroalkene-Michael addition to β-nitrostyrene analogues, showing broad substrate tolerance, high conversions and moderate to good asymmetric induction. The ability o

STABLE HEAVY ISOTOPES IN AMIDE FUNCTIONAL GROUPS AND USES THEREOF

-

Paragraph 00222, (2021/10/02)

There are provided isotope-enriched compounds containing stable heavy isotope-enriched amide functional groups for modulating the pharmacokinetic profile, metabolic profile, and/or delivery efficiency of a drug or prodrug, as well as its therapeutic or prophylactic efficacy and/or adverse effects. Use of the isotope-enriched amide-containing drugs and prodrugs for the treatment or prevention of disease states and conditions is also provided. (I)

Process route upstream and downstream products

Process route

O-(tert-butyl) S-(pyridin-2-yl)carbonothioate
105678-24-8

O-(tert-butyl) S-(pyridin-2-yl)carbonothioate

2-Sulfanylpyridine
2637-34-5,73018-10-7

2-Sulfanylpyridine

1-(tert-butoxycarbonyl)-L-proline
15761-39-4,59433-50-0

1-(tert-butoxycarbonyl)-L-proline

Conditions
Conditions Yield
With triethylamine; In water; N,N-dimethyl-formamide; for 4h; Ambient temperature;
95%
1,2,2,2-Tetrachloroethyl tert-Butyl Carbonate
98015-52-2

1,2,2,2-Tetrachloroethyl tert-Butyl Carbonate

1-(tert-butoxycarbonyl)-L-proline
15761-39-4,59433-50-0

1-(tert-butoxycarbonyl)-L-proline

chloral
75-87-6

chloral

Conditions
Conditions Yield
With triethylamine; In 1,4-dioxane; water; at 20 ℃; for 5h; Product distribution; var. amines, other 1-chloroalkyl carbonate, other basic reagent and time;
91%
1-(tert-butyl) 2-(2-oxo-2-phenylethyl) (S)-pyrrolidine-1,2-dicarboxylate
110345-80-7

1-(tert-butyl) 2-(2-oxo-2-phenylethyl) (S)-pyrrolidine-1,2-dicarboxylate

1-(tert-butoxycarbonyl)-L-proline
15761-39-4,59433-50-0

1-(tert-butoxycarbonyl)-L-proline

Conditions
Conditions Yield
With potassium phosphate; tris(2,2-bipyridine)ruthenium(II) hexafluorophosphate; ascorbic acid; In water; acetonitrile; at 20 ℃; for 2h; Irradiation;
100%
With ammonium formate; palladium on activated charcoal; In methanol; at 20 ℃; for 0.166667h;
95%
With magnesium; acetic acid; In methanol; N,N-dimethyl-formamide; at 20 ℃; for 75h;
tert-butyl (2,4-dioxo-3-azaspiro[5,5]undecan-3-yl) carbonate

tert-butyl (2,4-dioxo-3-azaspiro[5,5]undecan-3-yl) carbonate

1-(tert-butoxycarbonyl)-L-proline
15761-39-4,59433-50-0

1-(tert-butoxycarbonyl)-L-proline

Conditions
Conditions Yield
With triethylamine; In water; acetone; at 25 ℃; for 12h;
86%
C<sub>24</sub>H<sub>27</sub>NO<sub>5</sub>

C24H27NO5

1-(tert-butoxycarbonyl)-L-proline
15761-39-4,59433-50-0

1-(tert-butoxycarbonyl)-L-proline

Conditions
Conditions Yield
With potassium phosphate; tris(2,2-bipyridine)ruthenium(II) hexafluorophosphate; ascorbic acid; In water; acetonitrile; at 20 ℃; for 1h; Irradiation;
97%
N-(tert-butoxycarbonyl)-L-prolinol
69610-40-8

N-(tert-butoxycarbonyl)-L-prolinol

1-(tert-butoxycarbonyl)-L-proline
15761-39-4,59433-50-0

1-(tert-butoxycarbonyl)-L-proline

Conditions
Conditions Yield
With tert.-butylhydroperoxide; copper(l) chloride; In decane; acetonitrile; at 20 ℃;
59%
With chromium(VI) oxide; sulfuric acid; at 0 - 20 ℃; for 1h; Yield given;
With oxalyl dichloride; dimethyl sulfoxide; In dichloromethane; at -78 ℃; for 1h; Inert atmosphere;
allyl N-Boc-L-prolinate

allyl N-Boc-L-prolinate

1-(tert-butoxycarbonyl)-L-proline
15761-39-4,59433-50-0

1-(tert-butoxycarbonyl)-L-proline

Conditions
Conditions Yield
With polymethylhydrosiloxane; zinc(II) chloride; tetrakis(triphenylphosphine) palladium(0); In tetrahydrofuran; at 20 ℃;
85%
tert-butyldicarbonate
34619-03-9

tert-butyldicarbonate

1-(tert-butoxycarbonyl)-L-proline
15761-39-4,59433-50-0

1-(tert-butoxycarbonyl)-L-proline

Conditions
Conditions Yield
In water;
94%
With sodium hydroxide; In tetrahydrofuran;
85%
di-<i>tert</i>-butyl dicarbonate
24424-99-5

di-tert-butyl dicarbonate

(S)-N-benzyl-O-benzylpyrrolidine-2-carboxylate
83528-04-5

(S)-N-benzyl-O-benzylpyrrolidine-2-carboxylate

1-(tert-butoxycarbonyl)-L-proline
15761-39-4,59433-50-0

1-(tert-butoxycarbonyl)-L-proline

Conditions
Conditions Yield
With PMHS; palladium dihydroxide; In ethanol; at 20 ℃; for 5h;
86%
(S)-N-(tert-butoxycarbonyl)proline methyl ester
59936-29-7

(S)-N-(tert-butoxycarbonyl)proline methyl ester

1-(tert-butoxycarbonyl)-L-proline
15761-39-4,59433-50-0

1-(tert-butoxycarbonyl)-L-proline

Conditions
Conditions Yield
(S)-N-(tert-butoxycarbonyl)proline methyl ester; With sodium hydroxide; In methanol; water; for 5h; Reflux;
With hydrogenchloride; In water; pH=3;
98%
With lithium aluminium tetrahydride; In tetrahydrofuran; at 0 ℃;
97%
With lithium hydroxide; In tetrahydrofuran; methanol;
With lithium hydroxide; In 1,4-dioxane;

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