t-butyl (6S)-6-[(5'S)-5'-t-butyloxycarbonyl-2'-oxo-pyrrolidin-1'-yl]-3,6-dihydro-2H-1,2-oxazine-2-carboxylate

Base Information

• Chemical Name: t-butyl (6S)-6-[(5'S)-5'-t-butyloxycarbonyl-2'-oxo-pyrrolidin-1'-yl]-3,6-dihydro-2H-1,2-oxazine-2-carboxylate
• CAS No.: 529483-98-5
• Molecular Formula: C₁₈H₂₈N₂O₆
• Molecular Weight: 368.43
• Mol file: 529483-98-5.mol

Synonyms:t-butyl (6S)-6-[(5'S)-5'-t-butyloxycarbonyl-2'-oxo-pyrrolidin-1'-yl]-3,6-dihydro-2H-1,2-oxazine-2-carboxylate

Chemical Property of t-butyl (6S)-6-[(5'S)-5'-t-butyloxycarbonyl-2'-oxo-pyrrolidin-1'-yl]-3,6-dihydro-2H-1,2-oxazine-2-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of t-butyl (6S)-6-[(5'S)-5'-t-butyloxycarbonyl-2'-oxo-pyrrolidin-1'-yl]-3,6-dihydro-2H-1,2-oxazine-2-carboxylate

There total 3 articles about t-butyl (6S)-6-[(5'S)-5'-t-butyloxycarbonyl-2'-oxo-pyrrolidin-1'-yl]-3,6-dihydro-2H-1,2-oxazine-2-carboxylate 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:

tert-Butyl N-hydroxycarbamate (36016-38-3) + tert-butyl (5'S)-N-[1,3-butadienyl]-2'-oxopyrrolidine-5'-carboxylate → (R)-6-((S)-2-tert-Butoxycarbonyl-5-oxo-pyrrolidin-1-yl)-3,6-dihydro-[1,2]oxazine-2-carboxylic acid benzyl ester + t-butyl (6S)-6-[(5'S)-5'-t-butyloxycarbonyl-2'-oxo-pyrrolidin-1'-yl]-3,6-dihydro-2H-1,2-oxazine-2-carboxylate (529483-98-5)

Guidance literature:

tert-Butyl N-hydroxycarbamate; tert-butyl (5'S)-N-[1,3-butadienyl]-2'-oxopyrrolidine-5'-carboxylate; With Ru(S,S-iPr₂-pybox)(pydic); In methanol; for 0.0333333h;

With dihydrogen peroxide; In methanol; water; at 0 - 20 ℃; for 4h; Overall yield = 98 %; Overall yield = 109 mg; diastereoselective reaction;

DOI:10.2174/1570178614666170710101309

Reference yield:

L-t-butyl pyroglutamate (35418-16-7,85136-12-5) → (R)-6-((S)-2-tert-Butoxycarbonyl-5-oxo-pyrrolidin-1-yl)-3,6-dihydro-[1,2]oxazine-2-carboxylic acid benzyl ester + t-butyl (6S)-6-[(5'S)-5'-t-butyloxycarbonyl-2'-oxo-pyrrolidin-1'-yl]-3,6-dihydro-2H-1,2-oxazine-2-carboxylate (529483-98-5)

Guidance literature:

Multi-step reaction with 2 steps

1.1: toluene-4-sulfonic acid / toluene / 10 h / 100 °C / Molecular sieve

2.1: Ru(S,S-iPr₂-pybox)(pydic) / methanol / 0.03 h

2.2: 4 h / 0 - 20 °C

With Ru(S,S-iPr₂-pybox)(pydic); toluene-4-sulfonic acid; In methanol; toluene;

DOI:10.2174/1570178614666170710101309

Reference yield:

(S)-isopropyl 5-oxopyrrolidine-2-carboxylate (52989-50-1) → (R)-6-((S)-2-tert-Butoxycarbonyl-5-oxo-pyrrolidin-1-yl)-3,6-dihydro-[1,2]oxazine-2-carboxylic acid benzyl ester + t-butyl (6S)-6-[(5'S)-5'-t-butyloxycarbonyl-2'-oxo-pyrrolidin-1'-yl]-3,6-dihydro-2H-1,2-oxazine-2-carboxylate (529483-98-5)

Guidance literature:

Multi-step reaction with 3 steps

1.1: perchloric acid / water / 20 °C

2.1: toluene-4-sulfonic acid / toluene / 10 h / 100 °C / Molecular sieve

3.1: Ru(S,S-iPr₂-pybox)(pydic) / methanol / 0.03 h

3.2: 4 h / 0 - 20 °C

With perchloric acid; Ru(S,S-iPr₂-pybox)(pydic); toluene-4-sulfonic acid; In methanol; water; toluene;

DOI:10.2174/1570178614666170710101309

upstream raw materials:

tert-Butyl N-hydroxycarbamate

L-t-butyl pyroglutamate

(S)-isopropyl 5-oxopyrrolidine-2-carboxylate

Downstream raw materials:

L-t-butyl pyroglutamate