CID 11246553

Base Information

• Chemical Name: CID 11246553
• CAS No.: 112741-70-5
• Molecular Formula: C23H29NO5
• Molecular Weight: 399.487
• DSSTox Substance ID: DTXSID30460017
• Wikidata: Q82283921
• Mol file: 112741-70-5.mol

Synonyms:112741-70-5;Ethyl 2-((tert-butoxycarbonyl)((1S,2R)-2-hydroxy-1,2-diphenylethyl)amino)acetate;ethyl 2-[[(1S,2R)-2-hydroxy-1,2-diphenylethyl]-[(2-methylpropan-2-yl)oxycarbonyl]amino]acetate;N-(tert-Butyloxycarbonyl)-N-[(1S,2R)-2-hydroxy-1,2-diphenylethyl]-glycine Ethyl Ester;DTXSID30460017;AKOS016844903

Chemical Property of CID 11246553

Chemical Property:

• Melting Point: 60-62 °C
• Boiling Point: 518.5±50.0 °C(Predicted)
• PKA: 13.45±0.20(Predicted)
• PSA: 76.07000
• Density: 1.158±0.06 g/cm3(Predicted)
• LogP: 4.26150
• XLogP3: 3.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 10
• Exact Mass: 399.20457303
• Heavy Atom Count: 29
• Complexity: 518

Purity/Quality:

98%min ^*data from raw suppliers

N-(tert-Butyloxycarbonyl)-N-[(1S,2R)-2-hydroxy-1,2-diphenylethyl]-glycineEthylEster ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)CN(C(C1=CC=CC=C1)C(C2=CC=CC=C2)O)C(=O)OC(C)(C)C
• Isomeric SMILES: CCOC(=O)CN([C@@H](C1=CC=CC=C1)[C@@H](C2=CC=CC=C2)O)C(=O)OC(C)(C)C
• Uses: N-(tert-Butyloxycarbonyl)-N-[(1S,2R)-2-hydroxy-1,2-diphenylethyl]-glycine Ethyl Ester is a reactant used in the preparation of α-helixes of BCL-2 domains and collagen cross-linking agents such as (5S,5’S)-Dihydroxy Lysinonorleucine (D452900).

Technology Process of CID 11246553

There total 5 articles about CID 11246553 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: 85.0%

di-tert-butyl dicarbonate (24424-99-5) + 2-((1S,2R)-2-hydroxy-1,2-diphenylethylamino)acetic acid ethyl ester (100678-82-8) → (1'S,2'R)-ethyl N-(tert-butyloxycarbonyl)-N-(1',2'-diphenyl-2'-hydroxyethyl)glycinate (112741-70-5)

Guidance literature:

With sodium hydrogencarbonate; In chloroform; water; at 70 ℃; for 24h;

Reference yield:

(1R,2S)-2-Amino-1,2-diphenylethanol (23190-16-1) → (1'S,2'R)-ethyl N-(tert-butyloxycarbonyl)-N-(1',2'-diphenyl-2'-hydroxyethyl)glycinate (112741-70-5)

Guidance literature:

Multi-step reaction with 2 steps

1: Et₃N / tetrahydrofuran / 1 h / 20 °C

2: toluene / 10 h / Heating

With triethylamine; In tetrahydrofuran; toluene;

DOI:10.1055/s-2005-863740

Reference yield:

2-amino-1,2-diphenylethanol (530-36-9,3764-63-4,13286-63-0,23190-16-1,23190-17-2,23364-44-5,23412-95-5,39664-87-4,88082-66-0) → (1'S,2'R)-ethyl N-(tert-butyloxycarbonyl)-N-(1',2'-diphenyl-2'-hydroxyethyl)glycinate (112741-70-5)

Guidance literature:

Multi-step reaction with 3 steps

1.1: L-glutamic acid / ethanol / 72 °C

1.2: 90 °C

2.1: triethylamine / tetrahydrofuran / 20 °C

3.1: sodium hydrogencarbonate / chloroform; water / 24 h / 70 °C

With L-glutamic acid; sodium hydrogencarbonate; triethylamine; In tetrahydrofuran; ethanol; chloroform; water;

upstream raw materials:

di-tert-butyl dicarbonate

2-((1S,2R)-2-hydroxy-1,2-diphenylethylamino)acetic acid ethyl ester

(1R,2S)-2-Amino-1,2-diphenylethanol

2-amino-1,2-diphenylethanol

Downstream raw materials:

tert-butyl (2R,3S)-6-oxo-2,3-diphenylmorpholine-4-carboxylate

(3S,5S,6R)-4-(tert-butyloxycarbonyl)-5,6-diphenyl-3-(1'-prop-2'-enyl)-2,3,5,6-tetrahydro-4H-1,4-oxazin-2-one

(2S)-2-[(tert-butoxycarbonyl)amino]pent-4-enoic acid

(3S,5S,6R)-3-bromo-4(tert-butoxycarbonyl)-5,6-diphenyl-2,3,5,6-tetrahydro-4H-1,4-oxazin-2-one