Boc-L-PyroglutamicAcidTert-ButylEster

Base Information

• Chemical Name: Boc-L-PyroglutamicAcidTert-ButylEster
• CAS No.: 91237-84-2
• Molecular Formula: C14H25 N O4
• Molecular Weight: 271.357
• Mol file: 91237-84-2.mol

Synonyms:1,2-Pyrrolidinedicarboxylicacid, bis(1,1-dimethylethyl) ester, (2S)- (9CI); 1,2-Pyrrolidinedicarboxylicacid, bis(1,1-dimethylethyl) ester, (S)-; N-tert-Butoxycarbonyl-L-prolinetert-butyl ester

Chemical Property of Boc-L-PyroglutamicAcidTert-ButylEster

Chemical Property:

• PSA: 72.91000
• LogP: 2.19210

Purity/Quality:

98%Min ^*data from raw suppliers

Boc-Pyr-OtBu 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of Boc-L-PyroglutamicAcidTert-ButylEster

There total 2 articles about Boc-L-PyroglutamicAcidTert-ButylEster 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: 54.0%

N-benzyloxyacetamide (4797-81-3) + tert-butyl (S)-2-<(tert-butyloxycarbonyl)amino>-5-bromopentanoate (91229-86-6) → N-Boc-L-proline tert-butyl ester (91237-84-2) + 5-(N-Benzyloxy-acetimidoyloxy)-2-tert-butoxycarbonylamino-pentanoic acid tert-butyl ester (91229-89-9) + 5-(N-Benzyloxy-acetimidoyloxy)-2-tert-butoxycarbonylamino-pentanoic acid tert-butyl ester (91229-88-8) + α-tert-butyl Nα-(tert-butyloxycarbonyl)-Nδ-acetyl-Nδ-(benzyloxy)-L-ornithine (90195-02-1)

Guidance literature:

With potassium carbonate; potassium iodide; In acetone; for 24h; Heating;

DOI:10.1021/jo00193a016

Reference yield: 48.0%

C6H15N*C10H17NO4 (74108-10-4) + (S)-4-Benzyl-2-oxazolidinone (90719-32-7) + tert-butyl alcohol (75-65-0) → tert-butyl (S)-2-[(S)-4-benzyl-2-oxo-1,3-oxazolidin-3-ylcarbonyl]pyrrolidine-1-carboxylate (1260507-57-0) + N-BOC-proline tert-butyl ester (91237-84-2)

Guidance literature:

With dmap; dicyclohexyl-carbodiimide;

DOI:10.1055/s-0030-1258428

Reference yield: 98.0%

N-BOC-proline tert-butyl ester (91237-84-2) → L-proline (147-85-3,25191-13-3,37159-97-0,4305-67-3,4607-28-7)

Guidance literature:

With hydrogenchloride; In water; at 20 ℃; for 2h;

DOI:10.1016/j.tetlet.2005.04.126

upstream raw materials:

N-benzyloxyacetamide

tert-butyl (S)-2-<(tert-butyloxycarbonyl)amino>-5-bromopentanoate

C₆H₁₅N*C₁₀H₁₇NO₄

(S)-4-Benzyl-2-oxazolidinone

Downstream raw materials:

tert-butyl (S)-N-tert-butoxycarbonylpyroglutamate

L-proline tert-butyl ester hydrochloride

proline tert-butyl ester

L-proline

Refernces

• 1、 Olsen,Ramasamy,Emery. "Synthesis of N(α),N(δ)-protected N(δ)-hydroxy-L-ornithine from L-glutamic acid". . p. 3527 - 3534. Retrieved 2007/10/02.