(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

Base Information

• Chemical Name: (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
• CAS No.: 1257235-37-2
• Molecular Formula: C₃₉H₄₈FN₅O₆
• Molecular Weight: 701.838
• Mol file: 1257235-37-2.mol

Synonyms:(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

Chemical Property of (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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (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

There total 23 articles about (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 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-[6-(4-fluoro-benzyloxy)-hexahydro-pyrrolo[3,2-b]pyrrole-1-carbonyl]-2,2-dimethyl-propylcarbamoyl}-ethyl)-methyl-carbamic acid benzyl ester (1257235-35-0) + benzyl isothiocyanate (3173-56-6) → (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)

Guidance literature:

With triethylamine; In dichloromethane; at 20 ℃;

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) → (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)

Guidance literature:

Multi-step reaction with 7 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

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;

Reference yield:

N-Boc-4R-O-TBS-2R-aminoethyl-pyrrolidine (1245724-76-8) → (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)

Guidance literature:

Multi-step reaction with 19 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

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;

upstream raw materials:

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

benzyl isothiocyanate

(-)-(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

Downstream raw materials:

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