(6S,8R)-8-Azido-3-{[(benzyloxy)carbonyl][3-(trifluoromethyl)benzyl]amino}-8-methyl-4-oxo-4,6,7,8-tetrahydropyrrolo[1,2-a]pyrimidine-6-carboxylic acid

Base Information

• Chemical Name: (6S,8R)-8-Azido-3-{[(benzyloxy)carbonyl][3-(trifluoromethyl)benzyl]amino}-8-methyl-4-oxo-4,6,7,8-tetrahydropyrrolo[1,2-a]pyrimidine-6-carboxylic acid
• CAS No.: 437761-08-5
• Molecular Formula: C₂₅H₂₁F₃N₆O₅
• Molecular Weight: 542.474
• Mol file: 437761-08-5.mol

Synonyms:

Chemical Property of (6S,8R)-8-Azido-3-{[(benzyloxy)carbonyl][3-(trifluoromethyl)benzyl]amino}-8-methyl-4-oxo-4,6,7,8-tetrahydropyrrolo[1,2-a]pyrimidine-6-carboxylic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (6S,8R)-8-Azido-3-{[(benzyloxy)carbonyl][3-(trifluoromethyl)benzyl]amino}-8-methyl-4-oxo-4,6,7,8-tetrahydropyrrolo[1,2-a]pyrimidine-6-carboxylic acid

There total 8 articles about (6S,8R)-8-Azido-3-{[(benzyloxy)carbonyl][3-(trifluoromethyl)benzyl]amino}-8-methyl-4-oxo-4,6,7,8-tetrahydropyrrolo[1,2-a]pyrimidine-6-carboxylic acid 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: 100.0%

tert-Butyl (6S,8R)-(8-azido-3-{[(benzyloxy)carbonyl][3-(trifluoromethyl)benzyl]amino}-8-methyl-4-oxo-4,6,7,8-tetrahydropyrrolo[1,2-a]pyrimidin-6-yl)carbonyl(phenyl)carbamate (437761-07-4) → (6S,8R)-8-Azido-3-{[(benzyloxy)carbonyl][3-(trifluoromethyl)benzyl]amino}-8-methyl-4-oxo-4,6,7,8-tetrahydropyrrolo[1,2-a]pyrimidine-6-carboxylic acid (437761-08-5)

Guidance literature:

With lithium hydroxide; dihydrogen peroxide;

DOI:10.1016/S0960-894X(03)00022-2

Reference yield:

1-bromomethyl-3-trifluoromethylbenzene (402-23-3) → (6S,8R)-8-Azido-3-{[(benzyloxy)carbonyl][3-(trifluoromethyl)benzyl]amino}-8-methyl-4-oxo-4,6,7,8-tetrahydropyrrolo[1,2-a]pyrimidine-6-carboxylic acid (437761-08-5)

Guidance literature:

Multi-step reaction with 6 steps

1: NaH; TBAI

2: EDCI; HOAt; NaHCO₃

3: LiHMDS

4: LiHMDS; trisyl azide

5: 100 percent / DMAP / acetonitrile

6: 100 percent / aq. H₂O₂; LiOH

With dmap; lithium hydroxide; 1-hydroxy-7-aza-benzotriazole; 2,4,6-Triisopropylbenzenesulfonyl azide; dihydrogen peroxide; tetra-(n-butyl)ammonium iodide; sodium hydride; sodium hydrogencarbonate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; lithium hexamethyldisilazane; In acetonitrile;

DOI:10.1016/S0960-894X(03)00022-2

Reference yield:

(6S)-3-{[(Benzyloxy)carbonyl]amino}-4-oxo-4,6,7,8-tetrahydropyrrolo[1,2-a]pyrimidine-6-carboxylic acid (227616-77-5) → (6S,8R)-8-Azido-3-{[(benzyloxy)carbonyl][3-(trifluoromethyl)benzyl]amino}-8-methyl-4-oxo-4,6,7,8-tetrahydropyrrolo[1,2-a]pyrimidine-6-carboxylic acid (437761-08-5)

Guidance literature:

Multi-step reaction with 6 steps

1: NaH; TBAI

2: EDCI; HOAt; NaHCO₃

3: LiHMDS

4: LiHMDS; trisyl azide

5: 100 percent / DMAP / acetonitrile

6: 100 percent / aq. H₂O₂; LiOH

With dmap; lithium hydroxide; 1-hydroxy-7-aza-benzotriazole; 2,4,6-Triisopropylbenzenesulfonyl azide; dihydrogen peroxide; tetra-(n-butyl)ammonium iodide; sodium hydride; sodium hydrogencarbonate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; lithium hexamethyldisilazane; In acetonitrile;

DOI:10.1016/S0960-894X(03)00022-2

upstream raw materials:

tert-Butyl (6S,8R)-(8-azido-3-{[(benzyloxy)carbonyl][3-(trifluoromethyl)benzyl]amino}-8-methyl-4-oxo-4,6,7,8-tetrahydropyrrolo[1,2-a]pyrimidin-6-yl)carbonyl(phenyl)carbamate

1-bromomethyl-3-trifluoromethylbenzene

(6S)-3-{[(Benzyloxy)carbonyl]amino}-4-oxo-4,6,7,8-tetrahydropyrrolo[1,2-a]pyrimidine-6-carboxylic acid

(6S)-3-{[(Benzyloxy)carbonyl][3-(trifluoromethyl)benzyl]amino}-4-oxo-4,6,7,8-tetrahydropyrrolo[1,2-a]pyrimidine-6-carboxylic acid

Downstream raw materials:

{(6S,8R)-8-Azido-8-methyl-4-oxo-6-[(R)-1-((1S,2S,6R,8S)-2,9,9-trimethyl-3,5-dioxa-4-bora-tricyclo[6.1.1.0^2,6]dec-4-yl)-propylcarbamoyl]-4,6,7,8-tetrahydro-pyrrolo[1,2-a]pyrimidin-3-yl}-(3-trifluoromethyl-benzyl)-carbamic acid benzyl ester

(6S,8R)-8-Amino-8-methyl-4-oxo-3-(3-trifluoromethyl-benzylamino)-4,6,7,8-tetrahydro-pyrrolo[1,2-a]pyrimidine-6-carboxylic acid [(R)-1-((1S,2S,6R,8S)-2,9,9-trimethyl-3,5-dioxa-4-bora-tricyclo[6.1.1.0^2,6]dec-4-yl)-propyl]-amide