TERT-BUTYL 2-(TERT-BUTOXYCARBONYLAMINO)-6-(METHYLSULFONYLOXY)HEXANOATE

Base Information

• Chemical Name: TERT-BUTYL 2-(TERT-BUTOXYCARBONYLAMINO)-6-(METHYLSULFONYLOXY)HEXANOATE
• CAS No.: 878905-11-4
• Molecular Formula: C16H31NO7S
• Molecular Weight: 381.491
• Hs Code.: 2924199090
• Mol file: 878905-11-4.mol

Synonyms:Norleucine, N-[(1,1-dimethylethoxy)carbonyl]-6-[(methylsulfonyl)oxy]-, 1,1-dimethylethyl ester;

Chemical Property of TERT-BUTYL 2-(TERT-BUTOXYCARBONYLAMINO)-6-(METHYLSULFONYLOXY)HEXANOATE

Chemical Property:

• Vapor Pressure: 1.28E-10mmHg at 25°C
• Refractive Index: 1.471
• Boiling Point: 512.5 °C at 760 mmHg
• Flash Point: 263.8 °C
• PSA: 116.38000
• Density: 1.134 g/cm³
• LogP: 3.83960
• Storage Temp.: 2-8°C

Purity/Quality:

98.5% ^*data from raw suppliers

tert-Butyl 2-((tert-butoxycarbonyl)amino)-6-((methylsulfonyl)oxy)hexanoate 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of TERT-BUTYL 2-(TERT-BUTOXYCARBONYLAMINO)-6-(METHYLSULFONYLOXY)HEXANOATE

There total 4 articles about TERT-BUTYL 2-(TERT-BUTOXYCARBONYLAMINO)-6-(METHYLSULFONYLOXY)HEXANOATE 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: 100.0%

methanesulfonyl chloride (124-63-0) + (S)-(-)-tert-butyl-2-<(tert-butoxycarbonyl)amino>-6-hydroxyhexanoate (213176-15-9) → (S)-tert-butyl 2-tert-butoxycarbonylamino-6-methanesulfonylhexanoate (878905-11-4)

Guidance literature:

With pyridine; In dichloromethane; at 20 ℃; for 2h;

DOI:10.3987/COM-05-S(T)50

Reference yield:

N-tert-butoxycarbonyl glutamic acid tert-butyl ester (24277-39-2) → (S)-tert-butyl 2-tert-butoxycarbonylamino-6-methanesulfonylhexanoate (878905-11-4)

Guidance literature:

Multi-step reaction with 4 steps

1.1: EtO₂CCl; Et₃N / tetrahydrofuran / 0.83 h / -15 °C

1.2: 81 percent / tetrahydrofuran; diethyl ether / -15 - 20 °C

2.1: 56 percent / CF₃CO₂Ag; Et₃N / tetrahydrofuran; H₂O / 3 h / -10 °C

3.1: EtOCOCl; Et₃N / tetrahydrofuran / 1.17 h / -15 °C

3.2: 81 percent / NaBH₄ / tetrahydrofuran; H₂O / 2 h / 20 °C

4.1: 100 percent / pyridine / CH₂Cl₂ / 2 h / 20 °C

With pyridine; silver trifluoroacetate; chloroformic acid ethyl ester; triethylamine; In tetrahydrofuran; dichloromethane; water; 2.1: Wolff rearrangement;

DOI:10.3987/COM-05-S(T)50

Reference yield:

(S)-tert-butyl 2-tert-butoxycarbonylamino-6-hydroxycarbonyl-1-hexanoate (81323-62-8) → (S)-tert-butyl 2-tert-butoxycarbonylamino-6-methanesulfonylhexanoate (878905-11-4)

Guidance literature:

Multi-step reaction with 2 steps

1.1: EtOCOCl; Et₃N / tetrahydrofuran / 1.17 h / -15 °C

1.2: 81 percent / NaBH₄ / tetrahydrofuran; H₂O / 2 h / 20 °C

2.1: 100 percent / pyridine / CH₂Cl₂ / 2 h / 20 °C

With pyridine; chloroformic acid ethyl ester; triethylamine; In tetrahydrofuran; dichloromethane;

DOI:10.3987/COM-05-S(T)50

upstream raw materials:

methanesulfonyl chloride

(S)-(-)-tert-butyl-2-<(tert-butoxycarbonyl)amino>-6-hydroxyhexanoate

N-tert-butoxycarbonyl glutamic acid tert-butyl ester

(S)-tert-butyl 2-tert-butoxycarbonylamino-6-hydroxycarbonyl-1-hexanoate

Refernces

• 1、 Matsumoto, Kohsaku,Kumamoto, Takuya,Ishikawa, Tsutomu,Ishii, Erika,Tomitori, Hideyuki,Igarashi, Kazuei. "Preparation of Nα-acetyl-Nε-3-(methylpyridinium)lysine (MP-lysine) as a hapten of antibody". . p. 361 - 367. Retrieved 2007/10/03.