(S)-2-Amino-3-(2-benzyloxy-5-iodo-phenyl)-1-((1S,5R,7R)-10,10-dimethyl-3,3-dioxo-3λ⁶-thia-4-aza-tricyclo[5.2.1.0^1,5]dec-4-yl)-propan-1-one

Base Information

• Chemical Name: (S)-2-Amino-3-(2-benzyloxy-5-iodo-phenyl)-1-((1S,5R,7R)-10,10-dimethyl-3,3-dioxo-3λ⁶-thia-4-aza-tricyclo[5.2.1.0^1,5]dec-4-yl)-propan-1-one
• CAS No.: 616888-54-1
• Molecular Formula: C₂₆H₃₁IN₂O₄S
• Molecular Weight: 594.514

Synonyms:(S)-2-Amino-3-(2-benzyloxy-5-iodo-phenyl)-1-((1S,5R,7R)-10,10-dimethyl-3,3-dioxo-3λ⁶-thia-4-aza-tricyclo[5.2.1.0^1,5]dec-4-yl)-propan-1-one

Chemical Property of (S)-2-Amino-3-(2-benzyloxy-5-iodo-phenyl)-1-((1S,5R,7R)-10,10-dimethyl-3,3-dioxo-3λ⁶-thia-4-aza-tricyclo[5.2.1.0^1,5]dec-4-yl)-propan-1-one

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Technology Process of (S)-2-Amino-3-(2-benzyloxy-5-iodo-phenyl)-1-((1S,5R,7R)-10,10-dimethyl-3,3-dioxo-3λ⁶-thia-4-aza-tricyclo[5.2.1.0^1,5]dec-4-yl)-propan-1-one

There total 6 articles about (S)-2-Amino-3-(2-benzyloxy-5-iodo-phenyl)-1-((1S,5R,7R)-10,10-dimethyl-3,3-dioxo-3λ⁶-thia-4-aza-tricyclo[5.2.1.0^1,5]dec-4-yl)-propan-1-one 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: 95.0%

(S)-2-(Benzhydrylidene-amino)-3-(2-benzyloxy-5-iodo-phenyl)-1-((1S,5R,7R)-10,10-dimethyl-3,3-dioxo-3λ6-thia-4-aza-tricyclo[5.2.1.01,5]dec-4-yl)-propan-1-one (616888-53-0) → (S)-2-Amino-3-(2-benzyloxy-5-iodo-phenyl)-1-((1S,5R,7R)-10,10-dimethyl-3,3-dioxo-3λ6-thia-4-aza-tricyclo[5.2.1.01,5]dec-4-yl)-propan-1-one (616888-54-1)

Guidance literature:

With hydrogenchloride; In tetrahydrofuran; at 0 - 20 ℃;

DOI:10.1055/s-2003-37506

Reference yield:

2-hydroxy-5-iodobenzoic acid (119-30-2) → (S)-2-Amino-3-(2-benzyloxy-5-iodo-phenyl)-1-((1S,5R,7R)-10,10-dimethyl-3,3-dioxo-3λ6-thia-4-aza-tricyclo[5.2.1.01,5]dec-4-yl)-propan-1-one (616888-54-1)

Guidance literature:

Multi-step reaction with 5 steps

1.1: K₂CO₃ / dimethylformamide / 100 °C

2.1: DIBAL / CH₂Cl₂ / -78 - 20 °C

3.1: PBr₃ / toluene / 0 - 20 °C

4.1: n-BuLi / tetrahydrofuran / -78 °C

4.2: 84 percent / DMPU / tetrahydrofuran / -78 - 20 °C

5.1: 95 percent / aq. HCl / tetrahydrofuran / 0 - 20 °C

With hydrogenchloride; n-butyllithium; phosphorus tribromide; diisobutylaluminium hydride; potassium carbonate; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; toluene;

DOI:10.1055/s-2003-37506

Reference yield:

benzyl bromide (100-39-0) → (S)-2-Amino-3-(2-benzyloxy-5-iodo-phenyl)-1-((1S,5R,7R)-10,10-dimethyl-3,3-dioxo-3λ6-thia-4-aza-tricyclo[5.2.1.01,5]dec-4-yl)-propan-1-one (616888-54-1)

Guidance literature:

Multi-step reaction with 5 steps

1.1: K₂CO₃ / dimethylformamide / 100 °C

2.1: DIBAL / CH₂Cl₂ / -78 - 20 °C

3.1: PBr₃ / toluene / 0 - 20 °C

4.1: n-BuLi / tetrahydrofuran / -78 °C

4.2: 84 percent / DMPU / tetrahydrofuran / -78 - 20 °C

5.1: 95 percent / aq. HCl / tetrahydrofuran / 0 - 20 °C

With hydrogenchloride; n-butyllithium; phosphorus tribromide; diisobutylaluminium hydride; potassium carbonate; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; toluene;

DOI:10.1055/s-2003-37506

upstream raw materials:

(S)-2-(Benzhydrylidene-amino)-3-(2-benzyloxy-5-iodo-phenyl)-1-((1S,5R,7R)-10,10-dimethyl-3,3-dioxo-3λ⁶-thia-4-aza-tricyclo[5.2.1.0^1,5]dec-4-yl)-propan-1-one

2-hydroxy-5-iodobenzoic acid

benzyl bromide

2-benzyloxy-5-iodobenzoic acid

Downstream raw materials:

benzyl 3-(2-benzyloxy-5-iodophenyl)-2(S)-tert-butoxycarbonylaminopropionate

(-)-3-(2-benzyloxy-5-iodophenyl)-2(S)-tert-butoxycarbonylaminopropionic acid

(S)-2-benzyloxy-5-iodophenylalanine

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