Tert-butyl (2S)-3-amino-2-benzenesulfonamidopropanoate

Base Information

• Chemical Name: Tert-butyl (2S)-3-amino-2-benzenesulfonamidopropanoate
• CAS No.: 156185-89-6
• Molecular Formula: C13H20N2O4S
• Molecular Weight: 300.379
• DSSTox Substance ID: DTXSID401183974
• Mol file: 156185-89-6.mol

Synonyms:SCHEMBL7215705;FWNGNBTXQHWMHJ-NSHDSACASA-N;DTXSID401183974;156185-89-6;EN300-18980576;t-butyl(2s)-n-benzenesulfonyl-2,3-diaminopropionate;2(S)-phenylsulfonylamino-beta-alanine tert-butyl ester;3-Amino-N-(phenylsulfonyl)-L-alanine 1,1-dimethylethyl ester;TERT-BUTYL (2S)-3-AMINO-2-BENZENESULFONAMIDOPROPANOATE

Chemical Property of Tert-butyl (2S)-3-amino-2-benzenesulfonamidopropanoate

Chemical Property:

• XLogP3: 0.9
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 7
• Exact Mass: 300.11437830
• Heavy Atom Count: 20
• Complexity: 417

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)C(CN)NS(=O)(=O)C1=CC=CC=C1
• Isomeric SMILES: CC(C)(C)OC(=O)[C@H](CN)NS(=O)(=O)C1=CC=CC=C1

Technology Process of Tert-butyl (2S)-3-amino-2-benzenesulfonamidopropanoate

There total 3 articles about Tert-butyl (2S)-3-amino-2-benzenesulfonamidopropanoate 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: 55.5%

isobutene (115-11-7,15220-85-6) + 3-amino-2(S)-phenylsulfonylaminopropionic acid (156185-88-5) → tert-butyl (2S)-N-benzenesulfonyl-2,3-diaminopropionate (156185-89-6)

Guidance literature:

With sulfuric acid; In 1,2-dimethoxyethane; at -78 - 25 ℃; sealed tube;

DOI:10.1016/S0968-0896(98)00090-X

Reference yield:

N-phenylsulfonyl-L-asparagine (156185-87-4) → tert-butyl (2S)-N-benzenesulfonyl-2,3-diaminopropionate (156185-89-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 24 percent / aq. NaOH; Br₂ / 0.83 h / 0 - 90 °C

2: H₂SO₄ / 1,2-dimethoxy-ethane / 24 h / -78 °C

With sodium hydroxide; sulfuric acid; bromine; In 1,2-dimethoxyethane; 1: Hofmann degradation / 2: Addition;

DOI:10.1021/jm000133v

Reference yield:

benzenesulfonyl chloride (98-09-9) → tert-butyl (2S)-N-benzenesulfonyl-2,3-diaminopropionate (156185-89-6)

Guidance literature:

Multi-step reaction with 3 steps

1: 93 percent / aq. NaOH / dioxane / 0.5 h / 0 °C

2: 24 percent / aq. NaOH; Br₂ / 0.83 h / 0 - 90 °C

3: H₂SO₄ / 1,2-dimethoxy-ethane / 24 h / -78 °C

With sodium hydroxide; sulfuric acid; bromine; In 1,4-dioxane; 1,2-dimethoxyethane; 1: Condensation / 2: Hofmann degradation / 3: Addition;

DOI:10.1021/jm000133v

upstream raw materials:

isobutene

3-amino-2(S)-phenylsulfonylaminopropionic acid

N-phenylsulfonyl-L-asparagine

benzenesulfonyl chloride

Downstream raw materials:

2-benzenesulfonylamino-3-(4-fluoro-3-nitro-benzoylamino)-propionic acid tert-butyl ester

3-{4-[2-(pyrimidin-2-ylamino)ethyloxy]benzoylamino}-2(S)-benzenesulfonylaminopropionic acid tert-butyl ester

3-{4-[2-(N-BOC-amino)ethyloxy]benzoylamino}-2(S)-benzenesulfonylaminopropionic acid tert-butyl ester

3-[4-(2-aminopyridin-6-ylethyl)benzoylamino]-2(S)-benzenesulfonylaminopropionic acid tert-butyl ester