N-Boc-D-proline
- Product Name
- N-Boc-D-proline
- CAS No.
- 37784-17-1
- Chemical Name
- N-Boc-D-proline
- Synonyms
- BOC-D-PRO-OH;N-Boc-D-proline;BOC-D-PRO;BOC-D-PROLINE;N-Boc-D-proL;BOC-D-PYRD(2)-OH;BOC-D-PROLINE-OH;N-T-BOC-D-PROLINE;BOC-D-Proline,98%;N-BOC-D-PROLINE-OH
- CBNumber
- CB6404051
- Molecular Formula
- C10H17NO4
- Formula Weight
- 215.25
- MOL File
- 37784-17-1.mol
N-Boc-D-proline Property
- 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
- Safety Statements
- 24/25
- WGK Germany
- 3
- HS Code
- 2933 99 80
Hazard and Precautionary Statements (GHS)
- Symbol(GHS)
-
- Signal word
- Warning
- Hazard statements
-
H302Harmful if swallowed
H315Causes skin irritation
H319Causes serious eye irritation
H335May cause respiratory irritation
- Precautionary statements
-
P261Avoid breathing dust/fume/gas/mist/vapours/spray.
P280Wear protective gloves/protective clothing/eye protection/face protection.
P301+P312IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P302+P352IF ON SKIN: wash with plenty of soap and water.
P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.
N-Bromosuccinimide Price
- Product number
- 483818
- Product name
- N-Boc-D-proline
- Purity
- 99%
- Packaging
- 1g
- Price
- $29.26
- Updated
- 2025/07/31
- Product number
- 8.53095
- Product name
- Boc-D-Pro-OH
- Purity
- Novabiochem?
- Packaging
- 25g
- Price
- $630
- Updated
- 2025/07/31
- Product number
- 483818
- Product name
- N-Boc-D-proline
- Purity
- 99%
- Packaging
- 5g
- Price
- $131
- Updated
- 2025/07/31
- Product number
- B2977
- Product name
- N-(tert-Butoxycarbonyl)-D-proline
- Purity
- >98.0%(HPLC)(T)
- Packaging
- 5g
- Price
- $33
- Updated
- 2025/07/31
- Product number
- B2977
- Product name
- N-(tert-Butoxycarbonyl)-D-proline
- Purity
- >98.0%(HPLC)(T)
- Packaging
- 25g
- Price
- $68
- Updated
- 2025/07/31
N-Boc-D-proline Chemical Properties,Usage,Production
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
24424-99-5
344-25-2
37784-17-1
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 Preparation Products And Raw materials
Raw materials
Preparation Products
N-Boc-D-proline Suppliers
- Tel
- --
- Fax
- --
- sales21@chemicalland21.com
- Country
- South Korea
- ProdList
- 6303
- Advantage
- 74
View Lastest Price from N-Boc-D-proline manufacturers
- Product
- N-Boc-D-proline 37784-17-1
- Price
- US $0.00/Kg/Drum
- Min. Order
- 1KG
- Purity
- 98%min
- Supply Ability
- 500kgs
- Release date
- 2021-08-27
- Product
- Boc-D-Pro-OH 37784-17-1
- Price
- US $0.00-0.00/kg
- Min. Order
- 1kg
- Purity
- 98%
- Supply Ability
- 10
- Release date
- 2023-11-21
- Product
- N-Boc-D-proline 37784-17-1
- Price
- US $62.00/kg
- Min. Order
- 1kg
- Purity
- 99%
- Supply Ability
- 5000kg/week
- Release date
- 2024-05-24