(-)-(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

Base Information

• Chemical Name: (-)-(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
• CAS No.: 104849-07-2
• Molecular Formula: C₂₇H₃₇ClN₄O₅
• Molecular Weight: 533.068
• Mol file: 104849-07-2.mol

Synonyms:(-)-(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

Chemical Property of (-)-(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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (-)-(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

There total 15 articles about (-)-(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 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: 92.0%

S-{1-[(3S,9S,14aR)-9-benzyl-6,6-dimethyl-1,4,7,10-tetraoxotetradecahydropyrrolo[1,2-a][1,4,7,10]tetraazacyclododecin-3-yl]-7-chloro-6-oxoheptan-3-yl} O-ethyl carbonodithioate (1247052-85-2) → (-)-(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 (104849-07-2)

Guidance literature:

With dilauryl peroxide; isopropyl alcohol; for 5h; Reflux;

Reference yield:

(S)-2-(((benzyloxy)carbonyl)amino)-8-(tert-butoxy)-8-oxooctanoic acid (49645-27-4) → (-)-(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 (104849-07-2)

Guidance literature:

Multi-step reaction with 8 steps

1: Et₃N, N-(ethoxycarbonyl)-2-ethoxy-1,2-dihydroquinoline (EEDQ) / ethyl acetate / 27 h / 0 - 20 °C

2: 96 percent / 1.0 N aq. NaOH / methanol / Ambient temperature

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

4: 24 percent / Et₃N, bis(2-oxo-3-oxazolidinyl)phosphinic chloride (BOP-Cl) / CH₂Cl₂ / 64 h / -10 - 20 °C

5: TFA / CH₂Cl₂ / 1 h / Ambient temperature

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

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

8: HCl gas / diethyl ether; tetrahydrofuran / 1 h / Ambient temperature

With 4-methyl-morpholine; hydrogenchloride; sodium hydroxide; hydrogen; bis-(2-oxo-3-oxazolidinyl)phosphoryl chloride; N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline; triethylamine; trifluoroacetic acid; palladium on activated charcoal; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; ethyl acetate;

DOI:10.1021/jm00384a013

Reference yield:

N-(benzyloxycarbonyl)-L-2-amino-7-(tert-butyloxycarbonyl)heptanoyl-α-aminoisobutyryl-L-phenylalanyl-D-proline (104849-01-6) → (-)-(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 (104849-07-2)

Guidance literature:

Multi-step reaction with 6 steps

1: 94 percent / H₂ / 10percent Pd/C / methanol / 3 h

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

3: TFA / CH₂Cl₂ / 1 h / Ambient temperature

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

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

6: HCl gas / diethyl ether; tetrahydrofuran / 1 h / Ambient temperature

With 4-methyl-morpholine; hydrogenchloride; 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:

(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

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

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

cyclo

Downstream raw materials:

S-7-((3S,9S,14aR)-9-benzyl-6,6-dimethyl-1,4,7,10-tetraoxotetradecahydropyrrolo[1,2-a][1,4,7,10]tetraazacyclododecin-3-yl)-2-oxoheptyl O-ethyl carbonodithioate

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