D-1-N-Boc-prolinamide Chemical Properties

Melting point:

104-108 °C

Boiling point:

370.1±31.0 °C(Predicted)

Density 

1.155±0.06 g/cm3(Predicted)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

pka

15.97±0.20(Predicted)

form 

powder to crystal

color 

White to Almost white

optical activity

Consistent with structure

CAS DataBase Reference

35150-07-3(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xn

Risk Statements 

22

Safety Statements 

24/25

WGK Germany 

2

HS Code 

2933.99.9701

MSDS

• Language:English Provider:SigmaAldrich

D-1-N-Boc-prolinamide Usage And Synthesis

Chemical Properties

White to off-white powder

Uses

1-Boc-L-prolinamide is a reagent that is used in the preparation of thiazole amide peptidomimetics as erratum inhibitor apoptosis protein antagonist.

reaction suitability

reaction type: Boc solid-phase peptide synthesis

Synthesis

GENERAL METHOD: BOC-L-proline (1.00 g, 4.65 mmol), di-tert-butyl dicarbonate (1.52 g, 6.97 mmol), ammonium bicarbonate (0.55 g, 6.97 mmol), and pyridine (1.0 mL) were dissolved in dioxane (20 mL), and the reaction was stirred at room temperature for 6 hours. After completion of the reaction, the product was extracted with dichloromethane, the organic phase was washed sequentially with 1 M hydrochloric acid and saturated sodium chloride solution, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. To the concentrate was added n-hexane (100 mL) and sonication prompted the product to precipitate as a white solid to afford N-tert-butoxycarbonyl-L-prolinamide (0.85 g, 85% yield). The product was characterized by 1H NMR (300 MHz, CDCl3): δ 4.37-4.34 (m, 1H), 3.47-3.36 (m, 2H), 2.07-1.85 (m, 4H), 1.49 (s, 9H). Mass spectrum (ESI) m/z 215 [M + H]+.

References

[1] Bioorganic and Medicinal Chemistry, 2002, vol. 10, # 6, p. 1719 - 1729
[2] Canadian Journal of Chemistry, 2007, vol. 85, # 2, p. 85 - 95
[3] Journal of Agricultural and Food Chemistry, 2012, vol. 60, # 35, p. 8544 - 8551
[4] Journal of Medicinal Chemistry, 2017, vol. 60, # 1, p. 228 - 247
[5] Bioorganic and Medicinal Chemistry, 2013, vol. 21, # 23, p. 7418 - 7429

D-1-N-Boc-prolinamide(35150-07-3)Related Product Information

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• Cyhalofop-butyl
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• L-Prolinamide
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• Isobutyl chloroformate
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• RAC 1-METHYL-PYRROLIDINE-2-CARBONITRILE
• CHLOROAC-PRO-OH
• (S)-2-THIOCARBAMOYL-PYRROLIDINE-1-CARBOXYLIC ACID TERT-BUTYL ESTER
• Butyl acrylate
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