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BOC-L-Proline

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CAS:15761-39-4
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CAS:15761-39-4
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BOC-L-Proline Basic information
Product Name:BOC-L-Proline
Synonyms:BOC-L-PROLINE-OH;BOC-L-PRO;L-Proline, N-BOC protected, (2S)-1-(tert-Butoxycarbonyl)pyrrolidine-2-carboxylic acid;L-PROLINE-N-T-BOC;BOC-L-Proline, 99+% 25GR;(S)-1-(tert-buto×ycarbonyl)pyrrolidine-2-carbo×ylic acid N-Boc-L-Proline;N-Boc-L-proline Boc-Pro-OH;N-(tert-Butoxycarbonyl)-L-proline
CAS:15761-39-4
MF:C10H17NO4
MW:215.25
EINECS:239-848-3
Product Categories:Pyrrole&Pyrrolidine&Pyrroline;Protected Amino Acids;Proline [Pro, P];Boc-Amino Acids and Derivative;Amino Acids;Amino Acids (N-Protected);Biochemistry;Boc-Amino Acids;Boc-Amino acid series
Mol File:15761-39-4.mol
BOC-L-Proline Structure
BOC-L-Proline Chemical Properties
Melting point 133-135 °C(lit.)
alpha -60.5 º (c=1, HAc)
Boiling point 355.52°C (rough estimate)
density 1.1835 (rough estimate)
refractive index -60 ° (C=2, AcOH)
storage temp. Keep in dark place,Sealed in dry,Room Temperature
solubility Soluble in acetic acid.
pka4.01±0.20(Predicted)
form Crystals or Crystalline Powder
color White
Optical Rotation[α]20/D 61±2°, c = 2% in acetic acid
BRN 15828
Major Applicationpeptide synthesis
InChI1S/C10H17NO4/c1-10(2,3)15-9(14)11-6-4-5-7(11)8(12)13/h7H,4-6H2,1-3H3,(H,12,13)/t7-/m0/s1
InChIKeyZQEBQGAAWMOMAI-ZETCQYMHSA-N
SMILESCC(C)(C)OC(=O)N1CCC[C@H]1C(O)=O
CAS DataBase Reference15761-39-4(CAS DataBase Reference)
EPA Substance Registry System1,2-Pyrrolidinedicarboxylic acid, 1-(1,1-dimethylethyl) ester, (2S)- (15761-39-4)
Safety Information
Hazard Codes Xn
Risk Statements 20/21/22-36/37/38
Safety Statements 24/25-36-26
WGK Germany 3
TSCA TSCA listed
HS Code 2933 99 80
HazardClass IRRITANT
Storage Class11 - Combustible Solids
MSDS Information
BOC-L-Proline Usage And Synthesis
DescriptionN-Boc-L-proline is a synthetic intermediate. It has been used in the synthesis of enantioselective catalysts for aldol reactions and hepatitis C virus (HCV) NS5A inhibitors.
Chemical PropertiesWhite to off-white microcrystalline powder
UsesN-Boc-L-proline is used as an intermediate in organic synthesis. It is also used to prepare daclatasvir, which inhibits the hepatitis C virus (HCV) non-structural 5A (NS5A) protein. Further, it is used as a drug in the treatment of hepatitis C virus (HCV).
PreparationTriethylamine (16.5 mL, 0.12 mmol) was added dropwise over a period of 10 min to a stirred, ice-cold suspension of l-proline (10.0 g, 8.7 mmol) in dichloromethane (200 mL) in a 500-mL three-necked, round-bottomed flask. A solution of Boc2O (28.3 g, 0.13 mmol) in dichloromethane (100 mL) was then added over a period of 10 min and the mixture was stirred for 2.5 h. Thereafter, 10% aqueous citric acid (50 mL) was added, and the dichloromethane layer was washed with saturated brine (2×50 mL) and with water (50 mL). After drying the organic phase over magnesium sulfate, the solvent was evaporated and the residue was taken up in hot ethyl acetate. Dilution of this solution with hexane gave the product, N-tertbutoxycarbonyl- L-proline (17.8 g, 95%); mp 138–140℃; TLC (silica gel): Rf=0:36 (EtOAc/MeOH, 1:1).
reaction suitabilityreaction type: Boc solid-phase peptide synthesis
References[1] ALBRECHT BERKESSEL  Johann L  Burkhard Koch. Proline-Derived N-Sulfonylcarboxamides: Readily Available, Highly Enantioselective and Versatile Catalysts for Direct Aldol Reactions[J]. Advanced Synthesis & Catalysis, 2004, 346 9-10: 1141-1146. DOI: 10.1002/adsc.200404126
[2] JUNXING SHI . Synthesis and biological evaluation of new potent and selective HCV NS5A inhibitors[J]. Bioorganic & Medicinal Chemistry Letters, 2012, 22 10: Pages 3488-3491. DOI: 10.1016/j.bmcl.2012.03.089
Tag:BOC-L-Proline(15761-39-4) Related Product Information
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