| Identification | More | [Name]
N-Boc-D-proline | [CAS]
37784-17-1 | [Synonyms]
BOC-D-PRO
BOC-D-PROLINE
BOC-D-PROLINE-OH
BOC-D-PRO-OH
BOC-D-PYRD(2)-OH
BOC-(R)-PYRROLIDINE-5-CARBOXYLIC ACID
N-ALPHA-T-BOC-D-PROLINE
N-ALPHA-T-BUTYLOXYCARBONYL-D-PROLINE
N-ALPHA-T-BUTYLOXYCARBONYL-D-PYRROLIDINE-2-CARBOXYLIC ACID
N-ALPHA-TERT-BUTYLOXYCARBONYL-D-PROLINE
N-BOC-D-PROLINE
N-T-BOC-D-PROLINE
N-(TERT-BUTOXYCARBONYL)-D-PROLIN
N-(TERT-BUTOXYCARBONYL)-D-PROLINE
N-(TERT-BUTYLOXYCARBONYL)-D-PROLINE
(R)-PYRROLIDINE-1,2-DICARBOXYLIC ACID 1-TERT-BUTYL ESTER
T-BUTYLOXYCARBONYL-D-PROLINE
N-Boc-D-proline
N-BOC-D-PROLINE-OH
N-Boc-D-proline, 98+% | [EINECS(EC#)]
1533716-785-6 | [Molecular Formula]
C10H17NO4 | [MDL Number]
MFCD00063226 | [Molecular Weight]
215.25 | [MOL File]
37784-17-1.mol |
| Chemical Properties | Back Directory | [Appearance]
White to off-white microcrystalline powder | [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. ]
−20°C
| [solubility ]
almost transparency in Acetic acid | [form ]
Crystalline Powder or Crystals | [pka]
4.01±0.20(Predicted) | [color ]
White to off-white | [Optical Rotation]
[α]22/D +60°, c = 2 in acetic acid | [Detection Methods]
T,NMR,MS | [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) |
| Hazard Information | Back Directory | [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 |
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