(3S)-4-Benzyl-5-oxomorpholine-3-carboxylic acid

Base Information

• Chemical Name: (3S)-4-Benzyl-5-oxomorpholine-3-carboxylic acid
• CAS No.: 106973-37-9
• Molecular Formula: C12H13NO4
• Molecular Weight: 235.24
• Hs Code.: 2934999090
• Mol file: 106973-37-9.mol

Synonyms:3-Morpholinecarboxylicacid, 5-oxo-4-(phenylmethyl)-, (S)-;(3S)-4-Benzyl-5-oxomorpholine-3-carboxylicacid;

Chemical Property of (3S)-4-Benzyl-5-oxomorpholine-3-carboxylic acid

Chemical Property:

• Boiling Point: 506.8 °C at 760 mmHg
• Flash Point: 260.3 °C
• PSA: 66.84000
• Density: 1.339 g/cm³
• LogP: 0.43650
• Storage Temp.: Sealed in dry,Room Temperature

Purity/Quality:

97% ^*data from raw suppliers

(S)-4-Benzyl-5-oxomorpholine-3-carboxylicAcid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of (3S)-4-Benzyl-5-oxomorpholine-3-carboxylic acid

There total 4 articles about (3S)-4-Benzyl-5-oxomorpholine-3-carboxylic acid 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: 84.9%

(S)-2-(benzylamino)-3-hydroxypropanoic acid (106910-76-3,106910-77-4,17136-45-7) + chloroacetyl chloride (79-04-9) → (3S)-5-oxo-4-(phenylmethyl)-3-morpholinecarboxylic acid (106973-37-9)

Guidance literature:

(S)-2-(benzylamino)-3-hydroxypropanoic acid; chloroacetyl chloride; With potassium carbonate; In tetrahydrofuran; water; at 0 - 5 ℃; for 0.5h;

With sodium hydroxide; In tetrahydrofuran; water; at 5 - 10 ℃; pH=13.5;

With hydrogenchloride; In water; at -10 - 0 ℃; for 4h; pH=< 2;

Reference yield:

benzaldehyde (100-52-7) → (3S)-5-oxo-4-(phenylmethyl)-3-morpholinecarboxylic acid (106973-37-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 1) sodium hydroxide (2 M); 2) sodium borohydride / 1) 30 min; 2) 6-10 deg C, 1+1+1+2 h

2: 28 percent / sodium hydroxide / H₂O / 0 deg C, 30 min, 30-33 deg C, 2 h

With sodium hydroxide; sodium tetrahydroborate; In water;

Reference yield:

L-serin (56-45-1,83245-15-2) + benzaldehyde (100-52-7) + chloroacetyl chloride (79-04-9) → (3S)-5-oxo-4-(phenylmethyl)-3-morpholinecarboxylic acid (106973-37-9)

Guidance literature:

L-serin; benzaldehyde; With sodium hydroxide; In water; Large scale reaction;

With sodium tetrahydroborate; In water; Large scale reaction;

chloroacetyl chloride; Further stages;

DOI:10.1021/jm9010065

upstream raw materials:

(S)-2-(benzylamino)-3-hydroxypropanoic acid

chloroacetyl chloride

benzaldehyde

L-serin

Downstream raw materials:

(3R)-4-benzyl-3-(hydroxymethyl)-morpholine

(R)-(4-benzylmorpholin-3-yl)methanol hydrochloride

(3S)-N,N-dimethyl-5-oxo-4-phenylmethyl-3-morpholinecarboxamide

(3S)-5-oxo-N,4-bis(phenylmethyl)-3-morpholinecarboxamide