D-Serine, N-[(1,1-dimethylethoxy)carbonyl]-O-methyl- (9CI)

Base Information

• Chemical Name: D-Serine, N-[(1,1-dimethylethoxy)carbonyl]-O-methyl- (9CI)
• CAS No.: 86123-95-7
• Molecular Formula: C9H17NO5
• Molecular Weight: 219.238
• Hs Code.: 2924199090
• Mol file: 86123-95-7.mol

Synonyms:(2R)-3-methoxy-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoic acid

Chemical Property of D-Serine, N-[(1,1-dimethylethoxy)carbonyl]-O-methyl- (9CI)

Chemical Property:

• Refractive Index: 1.46
• Boiling Point: 355.8 °C at 760 mmHg
• PKA: 3.52±0.10(Predicted)
• Flash Point: 169 °C
• PSA: 84.86000
• Density: 1.149 g/cm³
• LogP: 1.00160
• Storage Temp.: 2-8°C

Purity/Quality:

98% ^*data from raw suppliers

Boc-O-methyl-D-serine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: Boc-O-methyl-D-serine is used in preparation of acylamino acid heterocyclyl amides and deuterated derivatives for the treatment of BAF complex-related disorders.

Technology Process of D-Serine, N-[(1,1-dimethylethoxy)carbonyl]-O-methyl- (9CI)

There total 12 articles about D-Serine, N-[(1,1-dimethylethoxy)carbonyl]-O-methyl- (9CI) which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

(R)-N-tert-butoxycarbonyl serine (3262-72-4,3850-40-6,6368-20-3,90582-28-8,84311-18-2) + dimethyl sulfate (77-78-1) → (R)-2-((tert-butoxycarbonyl)amino)-3-methoxypropionic acid (86123-95-7)

Guidance literature:

(R)-N-tert-butoxycarbonyl serine; With n-butyllithium; In tetrahydrofuran; hexane; at -10 - 5 ℃; for 1h;

dimethyl sulfate; In tetrahydrofuran; hexane; at 0 - 5 ℃; for 9h;

With sodium hydroxide; water; more than 3 stages; Product distribution / selectivity;

Reference yield: 100.0%

methyl (R)-2-(tert-butoxycarbonylamino)-3-methoxypropanoate (862372-14-3) → (R)-2-((tert-butoxycarbonyl)amino)-3-methoxypropionic acid (86123-95-7)

Guidance literature:

methyl (R)-2-(tert-butoxycarbonylamino)-3-methoxypropanoate; With lithium hydroxide; water; In tetrahydrofuran; at 20 ℃; for 4h;

With hydrogenchloride; In tetrahydrofuran; water; at 20 ℃;

Reference yield: 100.0%

(R)-N-tert-butoxycarbonyl serine (3262-72-4,3850-40-6,6368-20-3,90582-28-8,84311-18-2) + methyl p-toluene sulfonate (80-48-8) → (R)-2-((tert-butoxycarbonyl)amino)-3-methoxypropionic acid (86123-95-7)

Guidance literature:

(R)-N-tert-butoxycarbonyl serine; With potassium hydroxide; In toluene; at 0 - 5 ℃; for 0.5h;

methyl p-toluene sulfonate; With tetrabutylammomium bromide; In toluene; at 0 - 5 ℃; for 8h;

upstream raw materials:

(R)-N-tert-butoxycarbonyl serine

methyl iodide

methyl (R)-2-(tert-butoxycarbonylamino)-3-methoxypropanoate

methanol

Downstream raw materials:

(2R)-2-(tert-butoxycarbonyl-amino)-3-methoxy-N-[3-methyl-4-(3-oxo-morpholin-4-yl)-phenyl]-propionamide

(2R)-2-N-tert-butoxycarbonyl-amino-3-methoxy-propionic acid N'-[3-methyl-4-(pyrrolidin-1-yl-carbonyl)-phenyl]amide

tert-butyl [(2R)-1-(benzylamino)-3-methoxy-1-oxopropan-2-yl]carbamate

lacosamide

Refernces

• 1、 Yang, Anjiang,Hu, Feifei,Li, Zhong,Chen, Mengdi,Cai, Jianguang,Wang, Linghui,Zhang, Tao,Zhao, Chuanmeng,Zhang, Fuli. "Improved Synthesis and Impurity Identification of (R)-Lacosamide". . p. 818 - 824. Retrieved 2019/04/01.
• 2、 -. "A rakow amide preparation method". Paragraph 0140; 0141. . Retrieved 2016/10/17.