(R)-4-Benzyl-5-oxo-3-morpholinecarboxylic Acid
- Product Name
- (R)-4-Benzyl-5-oxo-3-morpholinecarboxylic Acid
- CAS No.
- 106973-36-8
- Chemical Name
- (R)-4-Benzyl-5-oxo-3-morpholinecarboxylic Acid
- Synonyms
- (R)-4-Benzyl-5-oxo-3-morpholinecarboxylic Acid;(3R)-4-Benzyl-5-oxomorpholine-3-carboxylic acid;(S)-5-oxo-4-(phenylMethyl)Morpholine-3-carboxylicacid;(3R)-5-oxo-4-(phenylmethyl)-3-Morpholinecarboxylic acid;3-Morpholinecarboxylic acid, 5-oxo-4-(phenylmethyl)-, (3R)-
- CBNumber
- CB32518207
- Molecular Formula
- C12H13NO4
- Formula Weight
- 235.24
- MOL File
- 106973-36-8.mol
(R)-4-Benzyl-5-oxo-3-morpholinecarboxylic Acid Property
- Melting point:
- 177-178 °C(Solv: isopropanol (67-63-0))
- Boiling point:
- 506.8±50.0 °C(Predicted)
- Density
- 1.339±0.06 g/cm3(Predicted)
- storage temp.
- Sealed in dry,Room Temperature
- pka
- 3.22±0.20(Predicted)
- Appearance
- White to off-white Solid
- optical activity
- -95.47° (C=1.00 g/100ml,1M NaOH)
- InChI
- InChI=1S/C12H13NO4/c14-11-8-17-7-10(12(15)16)13(11)6-9-4-2-1-3-5-9/h1-5,10H,6-8H2,(H,15,16)/t10-/m1/s1
- InChIKey
- LAHROJZLGLNLBT-SNVBAGLBSA-N
- SMILES
- N1(CC2=CC=CC=C2)C(=O)COC[C@@H]1C(O)=O
N-Bromosuccinimide Price
- Product number
- B285380
- Product name
- (R)-4-Benzyl-5-oxo-3-morpholinecarboxylicAcid
- Packaging
- 500mg
- Price
- $205
- Updated
- 2021/12/16
- Product number
- B285380
- Product name
- (R)-4-Benzyl-5-oxo-3-morpholinecarboxylicAcid
- Packaging
- 1g
- Price
- $285
- Updated
- 2021/12/16
- Product number
- CS-0038318
- Product name
- (3R)-4-Benzyl-5-oxomorpholine-3-carboxylicacid
- Packaging
- 25g
- Price
- $555
- Updated
- 2021/12/16
- Product number
- Z6914
- Product name
- (R)-4-Benzyl-5-oxo-3-morpholinecarboxylicacid
- Packaging
- 25g
- Price
- $637
- Updated
- 2021/12/16
- Product number
- CCH0012346
- Product name
- (R)-4-BENZYL-5-OXOMORPHOLINE-3-CARBOXYLIC ACID
- Purity
- 95.00%
- Packaging
- 5G
- Price
- $4966.5
- Updated
- 2021/12/16
(R)-4-Benzyl-5-oxo-3-morpholinecarboxylic Acid Chemical Properties,Usage,Production
Uses
(R)-4-Benzyl-5-oxo-3-morpholinecarboxylic Acid is a Morpholine (M723725) based compound that can be synthesized from Serine enantiomers and reduction of 5-oxomorpholine-3-carboxylates as key step.
Synthesis
106910-77-4
79-04-9
106973-36-8
The general procedure for the synthesis of (R)-4-benzyl-5-oxo-3-morpholinecarboxylic acid from (R)-2-(benzylamino)-3-hydroxypropanoic acid and chloroacetyl chloride was as follows: a 300-gallon Hastelloy reactor was charged with N-benzyl-D-serine (50.0 kg), followed by tetrahydrofuran (THF, 271.2 kg). The resulting solution was cooled to 0 °C and an aqueous solution (152.5 L) of potassium carbonate (53.1 kg) was added all at once while the temperature was controlled between -5 °C and 5 °C. The temperature was readjusted to 0 °C, followed by the addition of chloroacetyl chloride (40.2 kg) in batches over a period of 1 hour, ensuring that the temperature did not exceed 4 °C. The reaction mixture was stirred at 0-4 °C for 30 min and then another portion of chloroacetyl chloride (4.4 kg) was added in one go. Stirring was continued at 0-4°C for 30 minutes. A 50% aqueous sodium hydroxide solution (82.0 kg) was slowly added over 50 min while keeping the reaction temperature below 10 °C until the final pH reached 13-13.5. After addition, the solution was cooled to 3-5 °C and stirred at this temperature for 4 h. The reaction was then completed by HPLC. After confirming the completion of the reaction by HPLC, the mixture was warmed to 20-22°C, heptane (75.0 kg) was added and stirred vigorously. The basic aqueous layer was separated and collected, and after removing the heptane, the aqueous layer was re-poured into the reactor. The basic aqueous solution was again washed with heptane (107.8 kg) and then cooled to 30°C. Finally, 12N HCl (193.8 kg) was added in batches over a period of 1-1.5 hours for acidification.
References
[1] Patent: WO2011/23733, 2011, A1. Location in patent: Page/Page column 19-20
[2] Patent: WO2009/61879, 2009, A1. Location in patent: Page/Page column 85
[3] Patent: WO2013/82388, 2013, A1. Location in patent: Page/Page column 74-75
[4] Patent: US2008/300242, 2008, A1. Location in patent: Page/Page column 93
[5] Patent: WO2008/47109, 2008, A1. Location in patent: Page/Page column 40
(R)-4-Benzyl-5-oxo-3-morpholinecarboxylic Acid Preparation Products And Raw materials
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