(S)-3-BOC-AMINO-1-DIAZO-4-BENZYLOXY-2-BUTANONE

Base Information

• Chemical Name: (S)-3-BOC-AMINO-1-DIAZO-4-BENZYLOXY-2-BUTANONE
• CAS No.: 193148-60-6
• Molecular Formula: C16H21 N3 O4
• Molecular Weight: 319.36
• Mol file: 193148-60-6.mol

Synonyms:Carbamicacid, [3-diazo-2-oxo-1-[(phenylmethoxy)methyl]propyl]-, 1,1-dimethylethylester, (S)-

Chemical Property of (S)-3-BOC-AMINO-1-DIAZO-4-BENZYLOXY-2-BUTANONE

Chemical Property:

• PSA: 102.02000
• LogP: 2.43816

Purity/Quality:

98.5% ^*data from raw suppliers

(S)-3-BOC-AMINO-1-DIAZO-4-BENZYLOXY-2-BUTANONE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of (S)-3-BOC-AMINO-1-DIAZO-4-BENZYLOXY-2-BUTANONE

There total 4 articles about (S)-3-BOC-AMINO-1-DIAZO-4-BENZYLOXY-2-BUTANONE 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: 79.0%

diazomethane (186581-53-3,908094-01-9,334-88-3) + BOC-O-benzyl-L-serine (23680-31-1) → tert-butyl N-{(1S)-[(benzyloxy)methyl]-3-diazo-2-oxopropyl}carbamate (193148-60-6)

Guidance literature:

BOC-O-benzyl-L-serine; With chloroformic acid ethyl ester; triethylamine; In tetrahydrofuran; at -15 - 0 ℃; for 0.25h;

diazomethane; In tetrahydrofuran; diethyl ether; at 0 - 20 ℃; for 3h;

DOI:10.1002/1522-2675(20011017)84:10<2924::AID-HLCA2924>3.0.CO;2-E

Reference yield:

BOC-O-benzyl-L-serine (23680-31-1) → tert-butyl N-{(1S)-[(benzyloxy)methyl]-3-diazo-2-oxopropyl}carbamate (193148-60-6)

Guidance literature:

Multi-step reaction with 2 steps

1: NEt₃ / tetrahydrofuran / 0.25 h / -25 °C

2: tetrahydrofuran; diethyl ether / 3 h / Ambient temperature

With triethylamine; In tetrahydrofuran; diethyl ether;

DOI:10.1039/a805478i

Reference yield:

diazomethane (186581-53-3,908094-01-9,334-88-3) + C20H29NO7 (66866-45-3) → tert-butyl N-{(1S)-[(benzyloxy)methyl]-3-diazo-2-oxopropyl}carbamate (193148-60-6)

Guidance literature:

In diethyl ether; for 2h; Yield given; Ambient temperature;

DOI:10.1016/S0040-4039(98)00675-3

upstream raw materials:

diazomethane

C₂₀H₂₉NO₇

BOC-O-benzyl-L-serine

Downstream raw materials:

C₁₇H₂₂N₂O₄

C₂₈H₃₃N₅O₇

C₃₁H₃₉N₅O₇

C₁₉H₂₄N₄O₆

Refernces

• 1、 Pinho, Vagner D.,Gutmann, Bernhard,Kappe, C. Oliver. "Continuous flow synthesis of β-amino acids from α-amino acids via Arndt-Eistert homologation". . p. 37419 - 37422. Retrieved 2014/12/09.
• 2、 Vishwanathaa,Narendra,Sureshbabu, Vommina V.. "CuI-promoted one-pot synthesis of N-boc protected β-ketotriazole amino acids: Application in the synthesis of new class of dipeptidomimetics". . p. 308 - 314. Retrieved 2012/07/17.