N-(tert-Butoxycarbonyl)-(3S)-hydroxy-L-proline methyl ester
- Product Name
- N-(tert-Butoxycarbonyl)-(3S)-hydroxy-L-proline methyl ester
- CAS No.
- 184046-78-4
- Chemical Name
- N-(tert-Butoxycarbonyl)-(3S)-hydroxy-L-proline methyl ester
- Synonyms
- Methyl (2S,3S)-N-Boc-3-hydroxypyrrolidine-2-carboxylate;N-(tert-Butoxycarbonyl)-(3S)-hydroxy-L-proline methyl ester;(2S,3S)-1-(tert-Butoxycarbonyl)-3-Hydroxypyrrolidine-2-carboxyli;1-tert-butyl 2-methyl (2S,3S)-3-hydroxypyrrolidine-1,2-dicarboxylate;2-benzyl 1-(tert-butyl) (2S,3S)-3-hydroxypyrrolidine-1,2-dicarboxylate;(2s,3s)-3-hydroxy-1,2-pyrrolidinedicarboxylic acid 1-tert-butyl 2-methyl;1-(1,1-Dimethylethyl) 2-methyl (2S,3S)-3-hydroxy-1,2-pyrrolidinedicarboxylate;(2S,3S)-3-Hydroxy-1,2-pyrrolidinedicarboxylic acid 1-tert-butyl 2-methyl ester;(2S,3S)-1-(tert-Butoxycarbonyl)-3-hydroxypyrrolidine-2-carboxylic acid methyl ester;(2S,3S)-N-(tert-Butyloxycarbonyl)-3-hydroxy-2-pyrrolidinecarboxylic acid methyl ester
- CBNumber
- CB02510033
- Molecular Formula
- C11H19NO5
- Formula Weight
- 245.27
- MOL File
- 184046-78-4.mol
N-(tert-Butoxycarbonyl)-(3S)-hydroxy-L-proline methyl ester Property
- Boiling point:
- 335.2±42.0 °C(Predicted)
- Density
- 1.216
- storage temp.
- 2-8°C
- pka
- 14.03±0.40(Predicted)
- Appearance
- Light yellow to yellow Viscous liquid
- InChI
- InChI=1S/C11H19NO5/c1-11(2,3)17-10(15)12-6-5-7(13)8(12)9(14)16-4/h7-8,13H,5-6H2,1-4H3/t7-,8-/m0/s1
- InChIKey
- SVSSZFBZFUSINI-YUMQZZPRSA-N
- SMILES
- N1(C(OC(C)(C)C)=O)CC[C@H](O)[C@H]1C(OC)=O
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.
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
- H953490
- Product name
- (2S,3S)-3-Hydroxy-1,2-pyrrolidinedicarboxylicacid1-tert-Butyl2-MethylEster
- Packaging
- 25mg
- Price
- $165
- Updated
- 2021/12/16
- Product number
- B15057
- Product name
- (2S,3S)-1-(tert-Butoxycarbonyl)-3-Hydroxypyrrolidine-2-carboxylicacidmethylester
- Purity
- 95+%
- Packaging
- 250mg
- Price
- $280
- Updated
- 2021/12/16
- Product number
- B15057
- Product name
- (2S,3S)-1-(tert-Butoxycarbonyl)-3-Hydroxypyrrolidine-2-carboxylicacidmethylester
- Purity
- 95+%
- Packaging
- 500mg
- Price
- $570
- Updated
- 2021/12/16
- Product number
- B15057
- Product name
- (2S,3S)-1-(tert-Butoxycarbonyl)-3-Hydroxypyrrolidine-2-carboxylicacidmethylester
- Purity
- 95+%
- Packaging
- 1g
- Price
- $850
- Updated
- 2021/12/16
- Product number
- 125324
- Product name
- (2S,3S)-1-(tert-Butoxycarbonyl)-3-hydroxy-pyrrolidine-2-carboxylicacidmethylester
- Purity
- 95+%
- Packaging
- 1g
- Price
- $1552
- Updated
- 2021/12/16
N-(tert-Butoxycarbonyl)-(3S)-hydroxy-L-proline methyl ester Chemical Properties,Usage,Production
Uses
(2S,3S)-3-Hydroxy-1,2-pyrrolidinedicarboxylic acid 1-tert-butyl 2-methyl ester is a reactant used to improve potency of imidazo[1,2-b]pyridazines as IKKβ inhibitors.
Synthesis
187039-57-2
74-88-4
184046-78-4
GENERAL STEPS: A solution of DMF (100 mL) containing N-Boc-(2S,3S)-3-hydroxy-2-carboxypyrrolidine (37.16 g, 71 mmol) was cooled to 0°C. To this solution was added K2CO3 (16 g, 116 mmol) followed by slow dropwise addition of iodomethane (5.4 mL, 87 mmol). The reaction mixture was gradually warmed to room temperature over a period of 1 h. It was observed that the solution changed to a yellow non-homogeneous mixture. Next, the mixture was heated at 90 °C for 1 h, after which it was cooled to room temperature. After completion of the reaction, the reaction solution was diluted with saturated brine and extracted with ether. The organic phases were combined, dried with anhydrous Na2SO4, filtered and concentrated under reduced pressure to afford the target product (2S,3S)-1-(tert-butoxycarbonyl)-3-hydroxy-pyrrolidine-2-carboxylic acid methyl ester (14.8 g, 87% yield) as a yellow oil.
References
[1] Patent: US2008/20986, 2008, A1. Location in patent: Page/Page column 16
[2] Patent: WO2009/94287, 2009, A1. Location in patent: Page/Page column 31
[3] Patent: WO2010/138496, 2010, A1. Location in patent: Page/Page column 38-39
[4] Patent: WO2011/68926, 2011, A1. Location in patent: Page/Page column 39-40
[5] Patent: WO2010/33531, 2010, A1. Location in patent: Page/Page column 66
N-(tert-Butoxycarbonyl)-(3S)-hydroxy-L-proline methyl ester Preparation Products And Raw materials
Raw materials
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