D-Proline, 1-[N-[N-[8-(1,1-dimethylethoxy)-1,8-dioxo-2-[[(phenylmethoxy)carbonyl] amino]octyl]-2-methylalanyl]-L-phenylalanyl]-, methyl ester, (S)-

Base Information

• Chemical Name: D-Proline, 1-[N-[N-[8-(1,1-dimethylethoxy)-1,8-dioxo-2-[[(phenylmethoxy)carbonyl] amino]octyl]-2-methylalanyl]-L-phenylalanyl]-, methyl ester, (S)-
• CAS No.: 104874-88-6
• Molecular Formula: C39H54N4O9
• Molecular Weight: 722.879
• Mol file: 104874-88-6.mol

Synonyms:

Chemical Property of D-Proline, 1-[N-[N-[8-(1,1-dimethylethoxy)-1,8-dioxo-2-[[(phenylmethoxy)carbonyl] amino]octyl]-2-methylalanyl]-L-phenylalanyl]-, methyl ester, (S)-

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of D-Proline, 1-[N-[N-[8-(1,1-dimethylethoxy)-1,8-dioxo-2-[[(phenylmethoxy)carbonyl] amino]octyl]-2-methylalanyl]-L-phenylalanyl]-, methyl ester, (S)-

There total 1 articles about D-Proline, 1-[N-[N-[8-(1,1-dimethylethoxy)-1,8-dioxo-2-[[(phenylmethoxy)carbonyl] amino]octyl]-2-methylalanyl]-L-phenylalanyl]-, methyl ester, (S)- 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:

(S)-2-(((benzyloxy)carbonyl)amino)-8-(tert-butoxy)-8-oxooctanoic acid (49645-27-4) + (R)-1-[(S)-2-(2-Amino-2-methyl-propionylamino)-3-phenyl-propionyl]-pyrrolidine-2-carboxylic acid methyl ester; compound with trifluoro-acetic acid (104849-00-5) → N-(benzyloxycarbonyl)-L-2-amino-7-(tert-butyloxycarbonyl)heptanoyl-α-aminoisobutyryl-L-phenylalanyl-D-proline methyl ester (104874-88-6)

Guidance literature:

With N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline; triethylamine; In ethyl acetate; at 0 - 20 ℃; for 27h; Yield given;

DOI:10.1021/jm00384a013

Reference yield: 96.0%

N-(benzyloxycarbonyl)-L-2-amino-7-(tert-butyloxycarbonyl)heptanoyl-α-aminoisobutyryl-L-phenylalanyl-D-proline methyl ester (104874-88-6) → N-(benzyloxycarbonyl)-L-2-amino-7-(tert-butyloxycarbonyl)heptanoyl-α-aminoisobutyryl-L-phenylalanyl-D-proline (104849-01-6)

Guidance literature:

With sodium hydroxide; In methanol; Ambient temperature;

DOI:10.1021/jm00384a013

Reference yield:

N-(benzyloxycarbonyl)-L-2-amino-7-(tert-butyloxycarbonyl)heptanoyl-α-aminoisobutyryl-L-phenylalanyl-D-proline methyl ester (104874-88-6) → (5S,11S,13aR)-5-Benzyl-11-(7-diazo-6-oxo-heptyl)-8,8-dimethyl-decahydro-3a,6,9,12-tetraaza-cyclopentacyclododecene-4,7,10,13-tetraone (104849-06-1)

Guidance literature:

Multi-step reaction with 6 steps

1: 96 percent / 1.0 N aq. NaOH / methanol / Ambient temperature

2: 94 percent / H₂ / 10percent Pd/C / methanol / 3 h

3: 24 percent / Et₃N, bis(2-oxo-3-oxazolidinyl)phosphinic chloride (BOP-Cl) / CH₂Cl₂ / 64 h / -10 - 20 °C

4: TFA / CH₂Cl₂ / 1 h / Ambient temperature

5: N-methylmorpholine / tetrahydrofuran / 1 h / 0 - 20 °C

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

With 4-methyl-morpholine; sodium hydroxide; hydrogen; bis-(2-oxo-3-oxazolidinyl)phosphoryl chloride; triethylamine; trifluoroacetic acid; palladium on activated charcoal; In tetrahydrofuran; methanol; diethyl ether; dichloromethane;

DOI:10.1021/jm00384a013

upstream raw materials:

(S)-2-(((benzyloxy)carbonyl)amino)-8-(tert-butoxy)-8-oxooctanoic acid

(R)-1-[(S)-2-(2-Amino-2-methyl-propionylamino)-3-phenyl-propionyl]-pyrrolidine-2-carboxylic acid methyl ester; compound with trifluoro-acetic acid

Downstream raw materials:

N-(benzyloxycarbonyl)-L-2-amino-7-(tert-butyloxycarbonyl)heptanoyl-α-aminoisobutyryl-L-phenylalanyl-D-proline

cyclo[2-aminoisobutyryl-(S)-phenylalanyl-(R)-prolyl-(S)-2-aminosuberoyl-]

(-)-(3S,9S,14aR)-9-benzyl-3-(7-chloro-6-oxoheptyl)-6,6-dimethyldecahydropyrrolo[1,2-a][1,4,7,10]tetraazacyclododecine-1,4,7,10-tetraone

(5S,11S,13aR)-5-Benzyl-11-(7-diazo-6-oxo-heptyl)-8,8-dimethyl-decahydro-3a,6,9,12-tetraaza-cyclopentacyclododecene-4,7,10,13-tetraone