Carbamic acid, [(1S)-1-methyl-2-oxo-3-butynyl]-, 1,1-dimethylethyl ester (9CI)

Base Information

• Chemical Name: Carbamic acid, [(1S)-1-methyl-2-oxo-3-butynyl]-, 1,1-dimethylethyl ester (9CI)
• CAS No.: 97973-95-0
• Molecular Formula: C10H15 N O3
• Molecular Weight: 197.234
• Mol file: 97973-95-0.mol

Synonyms:Carbamicacid, (1-methyl-2-oxo-3-butynyl)-, 1,1-dimethylethyl ester, (S)-; Carbamicacid, [(1S)-1-methyl-2-oxo-3-butynyl]-, 1,1-dimethylethyl ester (9CI)

Chemical Property of Carbamic acid, [(1S)-1-methyl-2-oxo-3-butynyl]-, 1,1-dimethylethyl ester (9CI)

Chemical Property:

• PSA: 55.40000
• LogP: 1.49280

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of Carbamic acid, [(1S)-1-methyl-2-oxo-3-butynyl]-, 1,1-dimethylethyl ester (9CI)

There total 5 articles about Carbamic acid, [(1S)-1-methyl-2-oxo-3-butynyl]-, 1,1-dimethylethyl ester (9CI) 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: 80.0%

tert-butyl {(S)-1-[methoxy(methyl)amino]-1-oxopropan-2-yl}carbamate (146553-06-2,87694-49-3) + acetylenemagnesium bromide (4301-14-8) → 4-(S)-<(tert-butoxycarbonyl)amino>-1-pentyn-3-one (97973-95-0)

Guidance literature:

tert-butyl {(S)-1-[methoxy(methyl)amino]-1-oxopropan-2-yl}carbamate; acetylenemagnesium bromide; In tetrahydrofuran; at -78 - 20 ℃; for 13h; Inert atmosphere;

With sodium hydrogen sulfate; In tetrahydrofuran; water; at 0 ℃; for 1h; Inert atmosphere;

DOI:10.5560/ZNB.2014-4011

Reference yield: 72.0%

BOC-L-alanine-NCA (125814-30-4) + acetylenemagnesium bromide (4301-14-8) → 4-(S)-<(tert-butoxycarbonyl)amino>-1-pentyn-3-one (97973-95-0)

Guidance literature:

In tetrahydrofuran; at -60 - -40 ℃; for 4h;

DOI:10.1039/a809421g

Reference yield:

L-N-Boc-Ala (15761-38-3) → 4-(S)-<(tert-butoxycarbonyl)amino>-1-pentyn-3-one (97973-95-0)

Guidance literature:

Multi-step reaction with 3 steps

1: N-methylmorpholine / tetrahydrofuran / 0.02 h / -15 °C

2: Et₃N / dimethylformamide; tetrahydrofuran / 0.5 h / -15 °C

3: 1.) n-BuLi / 1.) THF, hexane, -78 deg C, 45 min, 2.) THF, hexane, from -78 deg C to 0 deg C, 30 min

With 4-methyl-morpholine; n-butyllithium; triethylamine; In tetrahydrofuran; N,N-dimethyl-formamide;

DOI:10.1021/jo00221a004

upstream raw materials:

N-(tert-butoxycarbonyl)-L-alanine isoxazolidide

acetylene

BOC-L-alanine-NCA

acetylenemagnesium bromide

Downstream raw materials:

methyl ((S,Z)-4-((tert-butoxycarbonyl)amino)-3-oxopent-1-en-1-yl)-L-tyrosinate

methyl ((S,E)-4-((tert-butoxycarbonyl)amino)-3-oxopent-1-en-1-yl)-L-tyrosinate

methyl ((S,Z)-4-((tert-butoxycarbonyl)amino)-3-oxopent-1-en-1-yl)-L-phenylalaninate

methyl ((S,E)-4-((tert-butoxycarbonyl)amino)-3-oxopent-1-en-1-yl)-L-phenylalaninate

Refernces

• 1、 Pusavec, Eva,Mirnik, Jona,Senica, Luka,Groselj, Uros,Stanovnik, Branko,Svete, Jurij. "Cu(I)-catalyzed [3+2] cycloadditions of tert-butyl (S)-(3-oxopent-4-yn-2- yl)carbamate to 1-benzylidenepyrazole-3-one-derived azomethine imines". . p. 615 - 626. Retrieved 2014/06/10.
• 2、 Cupps, Thomas L.,Boutin, Raymond H.,Rapoport, Henry. "α-Amino Acids as Chiral Educts for Asymmetric Products. The Synthesis of α'-Amino-α,β-ynones". . p. 3972 - 3979. Retrieved 2007/10/02.