(S)-4-METHYLENE-PYRROLIDINE-1,2-DICARBOXYLIC ACID 1-TERT-BUTYL ESTER
- Product Name
- (S)-4-METHYLENE-PYRROLIDINE-1,2-DICARBOXYLIC ACID 1-TERT-BUTYL ESTER
- CAS No.
- 84348-38-9
- Chemical Name
- (S)-4-METHYLENE-PYRROLIDINE-1,2-DICARBOXYLIC ACID 1-TERT-BUTYL ESTER
- Synonyms
- N-Boc-4-methylene-L-proline;(S)-1-(tert-butoxycarbonyl)-4-Methylenepyrrolidine-2-carboxylic acid;BOC-4-METHYLENE-L-PROLINE;4-Methylene-1-Boc-L-proline;N-T-BOC-4-METHYLENE-L-PROLINE;N-Boc-4-methylene-L-proline 97%;(2S)-N-Boc-4-methylene-L-proline;N-tert-Butoxycarbonyl-4-methylene-L-proline;N-Boc-4-methylene-
L -proline;1-Boc-(S)-4-Methylenepyrrolidine-2-carboxylic acid - CBNumber
- CB2176495
- Molecular Formula
- C11H17NO4
- Formula Weight
- 227.26
- MOL File
- 84348-38-9.mol
(S)-4-METHYLENE-PYRROLIDINE-1,2-DICARBOXYLIC ACID 1-TERT-BUTYL ESTER Property
- Melting point:
- 110-115 °C
- Boiling point:
- 349.9±42.0 °C(Predicted)
- Density
- 1.18±0.1 g/cm3 (20 ºC 760 Torr)
- storage temp.
- 2-8°C(protect from light)
- form
- solid
- pka
- 3.80±0.20(Predicted)
- Appearance
- Off-white to light yellow Solid
- optical activity
- [α]22/D 58°, c = 0.5 in chloroform
- Water Solubility
- Insoluble in water.
- CAS DataBase Reference
- 84348-38-9
Hazard and Precautionary Statements (GHS)
- Symbol(GHS)
-
- Signal word
- Warning
- Hazard statements
-
H315Causes skin irritation
H319Causes serious eye irritation
H335May cause respiratory irritation
- Precautionary statements
-
P261Avoid breathing dust/fume/gas/mist/vapours/spray.
P264Wash hands thoroughly after handling.
P264Wash skin thouroughly after handling.
P271Use only outdoors or in a well-ventilated area.
P280Wear protective gloves/protective clothing/eye protection/face protection.
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
- 717045
- Product name
- N-Boc-4-methylene-L-proline
- Purity
- 97%
- Packaging
- 500mg
- Price
- $123
- Updated
- 2023/06/20
- Product number
- M224740
- Product name
- 1-tert-ButylEster(S)-4-Methylene-pyrrolidine-1,2-dicarboxylicacid
- Packaging
- 500mg
- Price
- $90
- Updated
- 2021/12/16
- Product number
- 265607
- Product name
- Boc-4-methylene-L-proline
- Packaging
- 100mg
- Price
- $355
- Updated
- 2021/12/16
- Product number
- FB50569
- Product name
- Boc-4-methylene-L-proline
- Packaging
- 100mg
- Price
- $55
- Updated
- 2021/12/16
- Product number
- 16572
- Product name
- Boc-4-methylene-L-proline,≥99%(HPLC)
- Purity
- ≥99%(HPLC)
- Packaging
- 250MG
- Price
- $81.54
- Updated
- 2021/12/16
(S)-4-METHYLENE-PYRROLIDINE-1,2-DICARBOXYLIC ACID 1-TERT-BUTYL ESTER Chemical Properties,Usage,Production
Uses
As important intermediates in various areas such as peptide synthesis, asymmetric synthesis, medicinal chemistry, and polymer chemistry. The fluorous prolins were synthesized from commercially available N-Boc-4-methylene- L-proline.
reaction suitability
reaction type: Boc solid-phase peptide synthesis
Synthesis
1779-49-3
84348-37-8
84348-38-9
Example 2. Preparation of (S)-1-(tert-butoxycarbonyl)-4-methylenepyrrolidine-2-carboxylic acid To a suspension of methyltriphenylphosphonium bromide (236.4 g, 2.7 eq.) in tetrahydrofuran (1 L) was rapidly added potassium tert-butoxide (75.6 g, 2.75 eq.) at 0 °C. The reaction mixture was slowly warmed to room temperature and stirred for 2 hours, followed by cooling again to 0 °C. At this temperature, (S)-1-(tert-butoxycarbonyl)-4-oxopyrrolidine-2-carboxylic acid (56.2 g, 0.245 mol) was added batchwise keeping the reaction temperature below 5 °C. The reaction mixture was then cooled to room temperature and stirred for 2 hours. The reaction mixture was then warmed to room temperature and stirred overnight. Upon completion of the reaction, the mixture was cooled to 0 °C and the reaction was quenched with saturated sodium bicarbonate solution (500 mL) and water (200 mL). The solvent was removed by concentration under reduced pressure and the aqueous phase was extracted with tert-butyl methyl ether (2 x 400 mL). The aqueous phase was filtered through a diatomaceous earth pad, acidified with 6N hydrochloric acid (200 mL) and extracted with ethyl acetate (2 x 1 L). The organic phases were combined, washed with saturated brine, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The residue was dissolved in ethyl acetate (0.7 L) and extracted with 0.5N sodium hydroxide solution (0.7 L and 0.3 L). The aqueous phase was acidified with 6N hydrochloric acid (100 mL) and extracted with ethyl acetate (1 L and 0.8 L). The organic phases were combined, washed with saturated brine, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The residue was dissolved in a 50% ethyl acetate solution in cyclohexane (150 mL), and the solvent was slowly evaporated to give a pale yellow solid, which was filtered and dried to give (S)-1-(tert-butoxycarbonyl)-4-methylenepyrrolidine-2-carboxylic acid (26 g). The mother liquor was concentrated under reduced pressure to give the same light yellow solid, which was filtered and dried to give additional product (10 g). In total, 36 g of product (65% yield) was obtained as a white solid. In addition, the residue contained 18 g of product with 80% purity. 1H NMR (500 MHz, CDCl3): δ 5.04-5.02 (m, 2H), 4.53 (dd, J = 8.4, 3.2 Hz, 0.5H), 4.42 (d, J = 9.3 Hz, 0.5H), 4.09-3.98 (m, 2H), 3.05-2.69 (m, 2H), 1.49 and 1.43 (2s, 9H).
References
[1] Patent: WO2012/158861, 2012, A2. Location in patent: Page/Page column 19-20
[2] Patent: WO2010/43877, 2010, A1. Location in patent: Page/Page column 51; 52
[3] Patent: WO2007/25307, 2007, A2. Location in patent: Page/Page column 309
[4] Patent: WO2017/35353, 2017, A1. Location in patent: Paragraph 0759
[5] Patent: CN107954990, 2018, A. Location in patent: Paragraph 0080; 0082; 0083; 0153; 0222
(S)-4-METHYLENE-PYRROLIDINE-1,2-DICARBOXYLIC ACID 1-TERT-BUTYL ESTER Preparation Products And Raw materials
Raw materials
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View Lastest Price from (S)-4-METHYLENE-PYRROLIDINE-1,2-DICARBOXYLIC ACID 1-TERT-BUTYL ESTER manufacturers
- Product
- (S)-4-METHYLENE-PYRROLIDINE-1,2-DICARBOXYLIC ACID 1-TERT-BUTYL ESTER 84348-38-9
- Price
- US $0.00-0.00/g
- Min. Order
- 1g
- Purity
- 98%
- Supply Ability
- 100kg
- Release date
- 2023-06-30
- Product
- (S)-4-METHYLENE-PYRROLIDINE-1,2-DICARBOXYLIC ACID 1-TERT-BUTYL ESTER 84348-38-9
- Price
- US $100.00/KG
- Min. Order
- 1KG
- Purity
- 99%
- Supply Ability
- Customized
- Release date
- 2018-07-30