N-Boc-D-proline Chemical Properties

Melting point:

134-137 °C (lit.)

alpha 

60 º (c=2, acetic acid)

Boiling point:

355.52°C (rough estimate)

Density 

1.1835 (rough estimate)

refractive index 

60 ° (C=2, AcOH)

storage temp. 

2-8°C

solubility 

almost transparency in Acetic acid

form 

Crystalline Powder or Crystals

pka

4.01±0.20(Predicted)

color 

White to off-white

optical activity

[α]22/D +60°, c = 2 in acetic acid

BRN 

479316

InChI

InChI=1S/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-/m1/s1

InChIKey

ZQEBQGAAWMOMAI-SSDOTTSWSA-N

SMILES

N1(C(OC(C)(C)C)=O)CCC[C@@H]1C(O)=O

CAS DataBase Reference

37784-17-1(CAS DataBase Reference)

Safety Information

Safety Statements 

24/25

WGK Germany 

3

HS Code 

2933 99 80

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

N-Boc-D-proline Usage And Synthesis

Chemical Properties

White to off-white microcrystalline powder

Uses

tert-Butoxycarbonyl-D-proline is Boc protected D-proline (P755990). It is used to prepare trichostatin A and trapoxin B analogs as histone deacetylase inhibitors. It is also used to prepare potent and selective nonpeptide inhibitors of caspases 3 and 7.

reaction suitability

reaction type: Boc solid-phase peptide synthesis

Synthesis

Step-1: Synthesis of N-tert-butoxycarbonyl-(D)-proline: To a stirred solution of D-proline (100 g, 868.58 mmol) in dioxane (400 mL, 8 vol.) was added NaHCO3 (182.4 g, 2.5 equiv.) and water (800 mL, 8 vol.) and the reaction mixture was stirred for about 30 min at room temperature. The reaction mixture was cooled to 0-5 °C, di-tert-butyl dicarbonate (Boc2O) (224.26 g, 1.2 eq.) was slowly added and stirring was continued at 0-5 °C for 1 hour. Subsequently, the reaction mixture was gradually warmed to room temperature and stirred overnight (12-16 h). The progress of the reaction was monitored by thin layer chromatography (TLC). After completion of the reaction, the dioxane solvent was removed by evaporation under reduced pressure. The aqueous layer was acidified to pH 2-3 with 4N HCl solution at 0-5 °C. The aqueous layer was extracted with ethyl acetate (4 x 200 mL), the organic layers were combined, washed with water and dried with anhydrous Na2SO4. The organic layer was concentrated under reduced pressure to give a white solid product. The white solid was added to heptane (200 mL) and stirred at room temperature for 2 hours. The solid was collected by filtration and dried under vacuum at 45-50 °C to give the target compound (wt: 125 g, yield: 90-95%).1H NMR (300 MHz, CDCl3): δ 9.20 (br, 1H), 4.34 (t, 1H), 3.54-3.13 (m, 2H), 2.31-2.25 (m, 1H), 2.09- 1.88 (m, 3H), 1.48-1.42 (b, 9H); MS: [M + Na]+ 238 (100%).

References

[1] European Journal of Medicinal Chemistry, 2011, vol. 46, # 8, p. 3455 - 3461
[2] Patent: WO2014/105926, 2014, A1. Location in patent: Paragraph 0264
[3] Synthetic Communications, 2009, vol. 39, # 18, p. 3243 - 3253
[4] Journal of Medicinal Chemistry, 1998, vol. 41, # 3, p. 284 - 290
[5] Bioorganic and Medicinal Chemistry Letters, 2001, vol. 11, # 20, p. 2691 - 2696

N-Boc-D-proline(37784-17-1)Related Product Information

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