(S)-(-)-N-Boc-5-benzyl-2-oxomorpholine

Base Information

• Chemical Name: (S)-(-)-N-Boc-5-benzyl-2-oxomorpholine
• CAS No.: 130317-10-1
• Molecular Formula: C16H21 N O4
• Molecular Weight: 291.34
• European Community (EC) Number: 623-944-0
• DSSTox Substance ID: DTXSID80583821
• Wikidata: Q76511169
• Mol file: 130317-10-1.mol

Synonyms:(S)-(-)-N-Boc-5-benzyl-2-oxomorpholine;130317-10-1;tert-Butyl (5S)-5-benzyl-2-oxomorpholine-4-carboxylate;TERT-BUTYL (S)-(-)-5-BENZYL-2-OXO-4-;tert-Butyl (S)-5-benzyl-2-oxomorpholine-4-carboxylate;4-Morpholinecarboxylic acid, 2-oxo-5-(phenylmethyl)-, 1,1-dimethylethyl ester, (S)- (9CI);starbld0009164;DTXSID80583821;(S)-(-)-N-Boc-5-benzyl-2-oxomorpholine, 99%;J-005791

Chemical Property of (S)-(-)-N-Boc-5-benzyl-2-oxomorpholine

Chemical Property:

• Vapor Pressure: 5.6E-08mmHg at 25°C
• Melting Point: 98-100 °C(lit.)
• Refractive Index: 1.532
• Boiling Point: 441.1°Cat760mmHg
• Flash Point: 220.6°C
• PSA: 55.84000
• Density: 1.162g/cm³
• LogP: 2.32950
• XLogP3: 2.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 4
• Exact Mass: 291.14705815
• Heavy Atom Count: 21
• Complexity: 382

Purity/Quality:

99% ^*data from raw suppliers

(S)-(?)-N-Boc-5-benzyl-2-oxomorpholine 99% ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)N1CC(=O)OCC1CC2=CC=CC=C2
• Isomeric SMILES: CC(C)(C)OC(=O)N1CC(=O)OC[C@@H]1CC2=CC=CC=C2

Technology Process of (S)-(-)-N-Boc-5-benzyl-2-oxomorpholine

There total 1 articles about (S)-(-)-N-Boc-5-benzyl-2-oxomorpholine 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: 73.0%

di-tert-butyl dicarbonate (24424-99-5) + L-Phenylalaninol (3182-95-4) + ethyl bromoacetate (105-36-2) → 4-(tert-Butoxycarbonyl)-5S-benzyl-2H-1,4-oxazin-2-one (130317-10-1)

Guidance literature:

L-Phenylalaninol; ethyl bromoacetate; With triethylamine; In tetrahydrofuran; at 0 - 20 ℃; for 3h;

di-tert-butyl dicarbonate; In tetrahydrofuran; at 0 - 20 ℃;

With toluene-4-sulfonic acid; In tetrahydrofuran; toluene; for 5h; Reflux; Dean-Stark;

DOI:10.1002/anie.201800519

Reference yield:

4-(tert-Butoxycarbonyl)-5S-benzyl-2H-1,4-oxazin-2-one (130317-10-1) → Methyl 3-Aza-4(S)-benzyl-3-(tert-butoxycarbonyl)-2(S)-butyl-5-hydroxypentanoate (130317-17-8)

Guidance literature:

Multi-step reaction with 3 steps

1: 1) NaHMDS, HMPA

2: LiOH, H₂O / tetrahydrofuran / 24 h / Ambient temperature

With N,N,N,N,N,N-hexamethylphosphoric triamide; lithium hydroxide; water; sodium hexamethyldisilazane; In tetrahydrofuran;

DOI:10.1016/S0040-4039(00)91678-2

Reference yield:

4-(tert-Butoxycarbonyl)-5S-benzyl-2H-1,4-oxazin-2-one (130317-10-1) → (S)-2-[tert-Butoxycarbonyl-((S)-1-formyl-2-phenyl-ethyl)-amino]-hexanoic acid methyl ester

Guidance literature:

Multi-step reaction with 4 steps

1: 1) NaHMDS, HMPA

2: LiOH, H₂O / tetrahydrofuran / 24 h / Ambient temperature

4: Swern reagent

With N,N,N,N,N,N-hexamethylphosphoric triamide; lithium hydroxide; swern reagent; water; sodium hexamethyldisilazane; In tetrahydrofuran;

DOI:10.1016/S0040-4039(00)91678-2

upstream raw materials:

di-tert-butyl dicarbonate

L-Phenylalaninol

ethyl bromoacetate

Downstream raw materials:

(3S,5S)-5-Benzyl-3-((E)-but-2-enyl)-2-oxo-morpholine-4-carboxylic acid tert-butyl ester

(3S,5S)-5-Benzyl-3-(3-chloro-propyl)-2-oxo-morpholine-4-carboxylic acid tert-butyl ester

(3S,5S)-5-Benzyl-2-oxo-3-phenethyl-morpholine-4-carboxylic acid tert-butyl ester

(3R,5S)-5-Benzyl-3-(2,2-bis-benzenesulfonyl-ethyl)-2-oxo-morpholine-4-carboxylic acid tert-butyl ester

Refernces

• 1、 Baker, William R.,Condon, Stephen L.,Spanton, Stephen. "Synthesis and Structure Determination of (3S,5S)-2,3,5,6-Tetrahydro-3,5-dialkyl-N-(tert-butyloxycarbonyl)-4H-1,4-oxazine-2-ones". . p. 1573 - 1576. Retrieved 2007/10/02.