4-[3,3-dimethyl-2-(2-methylamino-propionylamino)-butyryl]-3-(4-fluorobenzyloxy)-hexahydro-pyrrolo[3,2-b]pyrrole-1-carboxylic acid benzylamide

Base Information

• Chemical Name: 4-[3,3-dimethyl-2-(2-methylamino-propionylamino)-butyryl]-3-(4-fluorobenzyloxy)-hexahydro-pyrrolo[3,2-b]pyrrole-1-carboxylic acid benzylamide
• CAS No.: 1257233-67-2
• Molecular Formula: C₃₁H₄₂FN₅O₄
• Molecular Weight: 567.704
• Mol file: 1257233-67-2.mol

Synonyms:4-[3,3-dimethyl-2-(2-methylamino-propionylamino)-butyryl]-3-(4-fluorobenzyloxy)-hexahydro-pyrrolo[3,2-b]pyrrole-1-carboxylic acid benzylamide

Chemical Property of 4-[3,3-dimethyl-2-(2-methylamino-propionylamino)-butyryl]-3-(4-fluorobenzyloxy)-hexahydro-pyrrolo[3,2-b]pyrrole-1-carboxylic acid benzylamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4-[3,3-dimethyl-2-(2-methylamino-propionylamino)-butyryl]-3-(4-fluorobenzyloxy)-hexahydro-pyrrolo[3,2-b]pyrrole-1-carboxylic acid benzylamide

There total 25 articles about 4-[3,3-dimethyl-2-(2-methylamino-propionylamino)-butyryl]-3-(4-fluorobenzyloxy)-hexahydro-pyrrolo[3,2-b]pyrrole-1-carboxylic acid benzylamide 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:

(1-{1-[4-benzylcarbamoyl-6-(4-fluoro-benzyloxy)-hexahydro-pyrrolo[3,2-b]pyrrole-1-carbonyl]-2,2-dimethyl-propylcarbamoyl}-ethyl)-methyl-carbamic acid benzyl ester (1257235-37-2) → 4-[3,3-dimethyl-2-(2-methylamino-propionylamino)-butyryl]-3-(4-fluorobenzyloxy)-hexahydro-pyrrolo[3,2-b]pyrrole-1-carboxylic acid benzylamide (1257233-67-2)

Guidance literature:

With ammonium acetate; hydrogen; palladium 10% on activated carbon; In methanol; for 1h;

Reference yield:

N-Boc-4R-O-TBS-2R-aminoethyl-pyrrolidine (1245724-76-8) → 4-[3,3-dimethyl-2-(2-methylamino-propionylamino)-butyryl]-3-(4-fluorobenzyloxy)-hexahydro-pyrrolo[3,2-b]pyrrole-1-carboxylic acid benzylamide (1257233-67-2)

Guidance literature:

Multi-step reaction with 20 steps

1.1: dichloromethane / 0 - 20 °C

2.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 0 °C

3.1: sulfur trioxide pyridine complex; triethylamine / dichloromethane; dimethyl sulfoxide / 0 - 20 °C

4.1: sodium hexamethyldisilazane / tetrahydrofuran / -78 °C

5.1: borane / tetrahydrofuran / -30 - 0 °C

5.2: -10 - 0 °C

6.1: N-ethyl-N,N-diisopropylamine / dmap / dichloromethane / 0 °C

7.1: hydrogen / palladium 10% on activated carbon / methanol / 3 h

8.1: sodium acetate / 85 - 90 °C

9.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 0 - 20 °C

10.1: pyridine hydrogenfluoride / tetrahydrofuran / 0 - 20 °C

11.1: di-isopropyl azodicarboxylate; triphenylphosphine / benzene / 20 °C

12.1: sodium hydroxide / tetrahydrofuran; methanol / 0 °C

13.1: sodium hydride / N,N-dimethyl-formamide / 0 °C

14.1: ammonium acetate; hydrogen / palladium 10% on activated carbon / methanol / 1.5 h

15.1: N-ethyl-N,N-diisopropylamine; HATU / 1-methyl-pyrrolidin-2-one / 0 - 20 °C

16.1: ammonium acetate; hydrogen / palladium 10% on activated carbon / methanol / 3 h

17.1: N-ethyl-N,N-diisopropylamine; HATU / 1-methyl-pyrrolidin-2-one / 0 - 20 °C

18.1: trifluoroacetic acid / dichloromethane / 0 °C

19.1: triethylamine / dichloromethane / 20 °C

20.1: ammonium acetate; hydrogen / palladium 10% on activated carbon / methanol / 1 h

With di-isopropyl azodicarboxylate; borane; ammonium acetate; tetrabutyl ammonium fluoride; hydrogen; sodium acetate; sodium hexamethyldisilazane; sulfur trioxide pyridine complex; sodium hydride; pyridine hydrogenfluoride; triethylamine; N-ethyl-N,N-diisopropylamine; triphenylphosphine; HATU; trifluoroacetic acid; sodium hydroxide; dmap; palladium 10% on activated carbon; In tetrahydrofuran; 1-methyl-pyrrolidin-2-one; methanol; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; benzene;

Reference yield:

(-)-(3S,3aS,6aR)-3-hydroxyhexahydropyrrolo[3,2-b]pyrrole-1,4-dicarboxylic acid 4-benzyl ester 1-tert-butyl ester (648930-90-9) → 4-[3,3-dimethyl-2-(2-methylamino-propionylamino)-butyryl]-3-(4-fluorobenzyloxy)-hexahydro-pyrrolo[3,2-b]pyrrole-1-carboxylic acid benzylamide (1257233-67-2)

Guidance literature:

Multi-step reaction with 8 steps

1: sodium hydride / N,N-dimethyl-formamide / 0 °C

2: ammonium acetate; hydrogen / palladium 10% on activated carbon / methanol / 1.5 h

3: N-ethyl-N,N-diisopropylamine; HATU / 1-methyl-pyrrolidin-2-one / 0 - 20 °C

4: ammonium acetate; hydrogen / palladium 10% on activated carbon / methanol / 3 h

5: N-ethyl-N,N-diisopropylamine; HATU / 1-methyl-pyrrolidin-2-one / 0 - 20 °C

6: trifluoroacetic acid / dichloromethane / 0 °C

7: triethylamine / dichloromethane / 20 °C

8: ammonium acetate; hydrogen / palladium 10% on activated carbon / methanol / 1 h

With ammonium acetate; hydrogen; sodium hydride; triethylamine; N-ethyl-N,N-diisopropylamine; HATU; trifluoroacetic acid; palladium 10% on activated carbon; In 1-methyl-pyrrolidin-2-one; methanol; dichloromethane; N,N-dimethyl-formamide;

upstream raw materials:

(1-{1-[4-benzylcarbamoyl-6-(4-fluoro-benzyloxy)-hexahydro-pyrrolo[3,2-b]pyrrole-1-carbonyl]-2,2-dimethyl-propylcarbamoyl}-ethyl)-methyl-carbamic acid benzyl ester

(-)-(3S,3aS,6aR)-3-hydroxyhexahydropyrrolo[3,2-b]pyrrole-1,4-dicarboxylic acid 4-benzyl ester 1-tert-butyl ester

N-Boc-4R-O-TBS-2R-aminoethyl-pyrrolidine

4-(tert-butyl-dimethyl-silanyloxy)-2-(2-nitro-vinyl)-pyrrolidine-1-carboxylic acid tert-butyl ester