(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

Base Information

• Chemical Name: (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
• CAS No.: 437761-12-1
• Molecular Formula: C₃₀H₃₉BF₃N₅O₄
• Molecular Weight: 601.477

Synonyms:(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

Chemical Property of (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

Chemical Property:

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Technology Process of (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

There total 10 articles about (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 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%

{(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[6.1.1.02,6]dec-4-yl)-propylcarbamoyl]-4,6,7,8-tetrahydro-pyrrolo[1,2-a]pyrimidin-3-yl}-(3-trifluoromethyl-benzyl)-carbamic acid benzyl ester (437761-09-6) → (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[6.1.1.02,6]dec-4-yl)-propyl]-amide (437761-12-1)

Guidance literature:

With hydrogen; palladium on activated charcoal; In methanol;

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

Reference yield:

1-bromomethyl-3-trifluoromethylbenzene (402-23-3) → (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[6.1.1.02,6]dec-4-yl)-propyl]-amide (437761-12-1)

Guidance literature:

Multi-step reaction with 8 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

7: EDCI; HOAt

8: 100 percent / H₂ / Pd/C / methanol

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

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

Reference yield:

(1R)-1-aminopropyl boronic acid pinanediol ester (208521-42-0) → (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[6.1.1.02,6]dec-4-yl)-propyl]-amide (437761-12-1)

Guidance literature:

Multi-step reaction with 2 steps

1: EDCI; HOAt

2: 100 percent / H₂ / Pd/C / methanol

With 1-hydroxy-7-aza-benzotriazole; hydrogen; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; palladium on activated charcoal; In methanol;

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

upstream 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

1-bromomethyl-3-trifluoromethylbenzene

(1R)-1-aminopropyl boronic acid pinanediol ester

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

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