Tert-butyl (2-amino-2-thioxoethyl)carbamate

Base Information

• Chemical Name: Tert-butyl (2-amino-2-thioxoethyl)carbamate
• CAS No.: 89226-13-1
• Molecular Formula: C7H14 N2 O2 S
• Molecular Weight: 190.266
• Hs Code.: 29309090
• European Community (EC) Number: 818-971-1
• DSSTox Substance ID: DTXSID30415901
• Nikkaji Number: J2.636.854E
• Mol file: 89226-13-1.mol

Synonyms:89226-13-1;tert-butyl (2-amino-2-thioxoethyl)carbamate;tert-Butyl 2-amino-2-thioxoethylcarbamate;tert-butyl N-(carbamothioylmethyl)carbamate;tert-butyl N-(2-amino-2-sulfanylideneethyl)carbamate;carbamic acid, (2-amino-2-thioxoethyl)-, 1,1-dimethylethyl ester;MFCD09025922;thiocarbamoylmethyl-carbamic acid tert-butyl ester;2-(Boc-amino)ethanethioamide;SCHEMBL1000974;DTXSID30415901;AKOS010592380;(tert-butoxycarbonylamino)acetothioamide;FS-4542;(N-t-butoxycarbonylamino) acetothioamide;(tert-butoxycarbonyl-amino)acetothioamide;2-(N-t-butoxycarbonylamino)thioacetamide;AM804506;SY173669;tert-butyl(2-amino-2-thioxoethyl)carbamate;CS-0092582;FT-0693971;tert-Butyl 2-amino-2-thioxoethylcarbamate #;2-[(tert-Butyloxycarbonyl)amino]thioacetamide;EN300-53880;tert-butyl n-(2-amino-2-thioxo-ethyl)carbamate;A843097;tert-Butyl (2-amino-2-sulfanylideneethyl)carbamate;F8889-9285;tert-butyl N-(2-azanyl-2-sulfanylidene-ethyl)carbamate;N-(2-amino-2-sulfanylideneethyl)carbamic acid tert-butyl ester;Carbamate, N-(2-amino-2-thioxoethyl)-, (1,1-dimethylethyl)ester;InChI=1/C7H14N2O2S/c1-7(2,3)11-6(10)9-4-5(8)12/h4H2,1-3H3,(H2,8,12)(H,9,10

Chemical Property of Tert-butyl (2-amino-2-thioxoethyl)carbamate

Chemical Property:

• Melting Point: 129 °C
• Refractive Index: 1.525
• PKA: 11.35±0.46(Predicted)
• PSA: 96.44000
• Density: 1.152g/cm³
• LogP: 1.88840
• Storage Temp.: 2-8°C
• XLogP3: 0.5
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 190.07759887
• Heavy Atom Count: 12
• Complexity: 186

Purity/Quality:

98%min ^*data from raw suppliers

tert-?Butyl2-?Amino-?2-?thioxoethylcarbamate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)NCC(=S)N
• Uses: tert-?Butyl 2-?Amino-?2-?thioxoethylcarbamate is a reactant used in the synthesis of polyazole peptide antibiotic Goadsporin which is a powerful antibiotic. Also used in the total synthesis of ME1036 which is a broad spectrum parenteral carbapenem.

Technology Process of Tert-butyl (2-amino-2-thioxoethyl)carbamate

There total 1 articles about Tert-butyl (2-amino-2-thioxoethyl)carbamate 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:

N-(tert-butoxycarbonyl)glycine methyl ester (31954-27-5) → 2-(N-t-butoxycarbonylamino)thioacetamide (89226-13-1)

Guidance literature:

Multi-step reaction with 2 steps

1: ammonium hydroxide / methanol / 6 h / Inert atmosphere; Sonication

2: Lawessons reagent / tetrahydrofuran / 20 °C / Inert atmosphere; Sealed tube

With Lawessons reagent; ammonium hydroxide; In tetrahydrofuran; methanol;

DOI:10.1021/acsmedchemlett.6b00488

Reference yield: 100.0%

2-(N-t-butoxycarbonylamino)thioacetamide (89226-13-1) + 4-chlorobenzoylmethyl bromide (536-38-9) → [4-(4-chlorophenyl)thiazol-2-yl]methylamine hydrochloride

Guidance literature:

2-(N-t-butoxycarbonylamino)thioacetamide; 4-chlorobenzoylmethyl bromide; In ethanol; at 20 ℃;

With hydrogenchloride; In 1,4-dioxane; ethanol; at 20 ℃; for 2h;

Reference yield: 70.0%

2-bromophenyl methyl ketone (2142-69-0) + 2-(N-t-butoxycarbonylamino)thioacetamide (89226-13-1) → tert-butyl N-[(4-phenylthiazol-2-yl)methyl]carbamate

Guidance literature:

In ethanol; at 20 ℃; for 16h;

upstream raw materials:

N-(tert-butoxycarbonyl)glycine methyl ester

Downstream raw materials:

2-((tert-butoxycarbonylamino)methyl)thiazole-4-carboxylic acid

Glycin-thioamid-hyrochlorid

2-((S)-1-{[2-((R)-1-{[2-(tert-Butoxycarbonylamino-methyl)-thiazole-4-carbonyl]-amino}-2-methyl-propyl)-thiazole-4-carbonyl]-amino}-ethyl)-5-methyl-oxazole-4-carboxylic acid pentafluorophenyl ester

(2S,4R)-2-[2-(N-t-butoxycarbonylamino)methylthiazol-4-yl]-4-methanesulfonyloxy-1-(4-nitrobenzyloxycarbonyl)pyrrolidine

Refernces