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BOC-DL-PRO-OH, also known as (±)-N-(tert-Butoxycarbonyl)proline, is a chemical compound that serves as a useful reagent in the synthesis of various organic compounds. It is a derivative of proline, an essential amino acid, with a tert-butoxycarbonyl (BOC) protecting group attached to the nitrogen atom. This modification enhances the stability and reactivity of the compound during chemical reactions.

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  • 59433-50-0 Structure
  • Basic information

    1. Product Name: BOC-DL-PRO-OH
    2. Synonyms: PYRROLIDINE-1,2-DICARBOXYLIC ACID 1-TERT-BUTYL ESTER;BOC-DL-PROLINE;BOC-DL-PRO-OH;1-(TERT-BUTOXYCARBONYL)PYRROLIDINE-2-CARBOXYLIC ACID;AKOS 91525;N-BOC-DL-PROLINE;REF DUPL: Boc-DL-Pro-OH;1-(tert-butoxycarbonyl)proline [Boc-DL-Pro-OH]
    3. CAS NO:59433-50-0
    4. Molecular Formula: C10H17NO4
    5. Molecular Weight: 215.25
    6. EINECS: N/A
    7. Product Categories: Boc-Amino Acids and Derivative;Boc-Amino acid series;Boc Amino Acids
    8. Mol File: 59433-50-0.mol
  • Chemical Properties

    1. Melting Point: 133-135°C
    2. Boiling Point: 337.2 °C at 760 mmHg
    3. Flash Point: 157.7 °C
    4. Appearance: /
    5. Density: 1.201 g/cm3
    6. Refractive Index: N/A
    7. Storage Temp.: 2-8°C
    8. Solubility: N/A
    9. PKA: 4.01±0.20(Predicted)
    10. CAS DataBase Reference: BOC-DL-PRO-OH(CAS DataBase Reference)
    11. NIST Chemistry Reference: BOC-DL-PRO-OH(59433-50-0)
    12. EPA Substance Registry System: BOC-DL-PRO-OH(59433-50-0)
  • Safety Data

    1. Hazard Codes: N/A
    2. Statements: N/A
    3. Safety Statements: N/A
    4. WGK Germany:
    5. RTECS:
    6. HazardClass: IRRITANT
    7. PackingGroup: N/A
    8. Hazardous Substances Data: 59433-50-0(Hazardous Substances Data)

59433-50-0 Usage

Uses

Used in Pharmaceutical Industry:
BOC-DL-PRO-OH is used as a reagent for the enantiospecific preparation of functionalized hindered triazolopyridinones. These triazolopyridinones are important intermediates in the synthesis of pharmaceutical compounds with potential therapeutic applications. The enantiospecific preparation ensures that the desired chiral centers are correctly formed, leading to the production of biologically active molecules.

Check Digit Verification of cas no

The CAS Registry Mumber 59433-50-0 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 5,9,4,3 and 3 respectively; the second part has 2 digits, 5 and 0 respectively.
Calculate Digit Verification of CAS Registry Number 59433-50:
(7*5)+(6*9)+(5*4)+(4*3)+(3*3)+(2*5)+(1*0)=140
140 % 10 = 0
So 59433-50-0 is a valid CAS Registry Number.

59433-50-0 Well-known Company Product Price

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  • Alfa Aesar

  • (H32347)  N-Boc-DL-proline, 98%   

  • 59433-50-0

  • 250mg

  • 431.0CNY

  • Detail
  • Alfa Aesar

  • (H32347)  N-Boc-DL-proline, 98%   

  • 59433-50-0

  • 1g

  • 1196.0CNY

  • Detail
  • Alfa Aesar

  • (H32347)  N-Boc-DL-proline, 98%   

  • 59433-50-0

  • 5g

  • 3979.0CNY

  • Detail

59433-50-0SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 15, 2017

Revision Date: Aug 15, 2017

1.Identification

1.1 GHS Product identifier

Product name N-Boc-DL-proline

1.2 Other means of identification

Product number -
Other names 1-(tert-Butoxycarbonyl)pyrrolidine-2-carboxylic acid

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:59433-50-0 SDS

59433-50-0Relevant articles and documents

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)

RAS INHIBITORS

-

Paragraph 1184-1185, (2021/05/07)

The disclosure features macrocyclic compounds, and pharmaceutical compositions and protein complexes thereof, capable of inhibiting Ras proteins, and their uses in the treatment of cancers.

METHODS FOR DELAYING, PREVENTING, AND TREATING ACQUIRED RESISTANCE TO RAS INHIBITORS

-

Page/Page column 342-343, (2022/01/04)

The present disclosure relates to compositions and methods for the treatment of diseases or disorders (e.g., cancer) with bi-steric inhibitors of mTOR in combination with RAS inhibitors. Specifically, in some embodiments this disclosure includes compositions and methods for inducing apoptosis of tumor cells and/or for delaying, preventing, or treating acquired resistance to RAS inhibitors using bi-steric mTOR inhibitors.

A Facile Approach to the Synthesis of Benzothiazoles from N-Protected Amino Acids

Arfan, M.,Fatima, T.,Mannan, A.,Tahira, A.

, p. 292 - 297 (2020/04/21)

Abstract: –A simple trituration method for the synthesis of 2-substituted benzothiazoles derived from N-protected amino acids and 2-aminothiophenol using molecular iodine as a mild Lewis acid catalyst has been proposed. The reaction occurs in one step for 20–25 min in solve-free conditions and provides the target products in excellent yields.

Design and preparation of a novel prolinamide-based organocatalyst for the solvent-free asymmetric aldol reaction

Martins, Rafaela de S.,Pereira, Mathias P.,de Castro, Pedro P.,Bombonato, Fernanda I.

, (2019/12/24)

The preparation of four novel organocatalysts as highly diastereo and enantioselective catalysts for the solvent-free asymmetric aldol reaction was described. These organocatalysts were synthesized in eight steps applying simple and commercially available starting materials. The best results were obtained for the proline-derived catalyst, providing access to the desired adducts in up to 95% yield, 1:19 syn/anti and 98% e.e. Moreover, even sterically bulky aldehydes and substituted cyclohexanones were well tolerated. DFT calculations and control experiments indicated that several hydrogen bonding interactions between the aldehyde and the enamine intermediate are responsible for the stereoselective chiral induction process and that the trifluoroacetate counter-anion is crucial for the attainment of higher stereoselectivities.

Composition for promoting differentiation of skin keratinocyte comprising a SAC derivatives or a SMC derivatives

-

Paragraph 0086-0089; 0099-0101; 0111-0114; 0124-0126, (2021/02/02)

The present invention relates to a composition for promoting keratinocyte differentiation. More specifically, SAC derivative or SMC derivatives as an active ingredient promotes differentiation of keratinocytes to promote skin keratinocyte differentiation, has excellent anti-wrinkling effect, skin barrier recovery effect, and is applicable to pharmaceutical, cosmetic, soap, body, shampoo and pack.

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