(Z)-(R)-2-(Benzhydrylidene-amino)-4-((1S,5R,7R)-10,10-dimethyl-3,3-dioxo-3λ⁶-thia-4-aza-tricyclo[5.2.1.0^1,5]decane-4-carbonyl)-hex-2-enedioic acid 1-tert-butyl ester 6-ethyl ester

Base Information

• Chemical Name: (Z)-(R)-2-(Benzhydrylidene-amino)-4-((1S,5R,7R)-10,10-dimethyl-3,3-dioxo-3λ⁶-thia-4-aza-tricyclo[5.2.1.0^1,5]decane-4-carbonyl)-hex-2-enedioic acid 1-tert-butyl ester 6-ethyl ester
• CAS No.: 342376-62-9
• Molecular Formula: C₃₆H₄₄N₂O₇S
• Molecular Weight: 648.821

Synonyms:(Z)-(R)-2-(Benzhydrylidene-amino)-4-((1S,5R,7R)-10,10-dimethyl-3,3-dioxo-3λ⁶-thia-4-aza-tricyclo[5.2.1.0^1,5]decane-4-carbonyl)-hex-2-enedioic acid 1-tert-butyl ester 6-ethyl ester

Chemical Property of (Z)-(R)-2-(Benzhydrylidene-amino)-4-((1S,5R,7R)-10,10-dimethyl-3,3-dioxo-3λ⁶-thia-4-aza-tricyclo[5.2.1.0^1,5]decane-4-carbonyl)-hex-2-enedioic acid 1-tert-butyl ester 6-ethyl ester

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Technology Process of (Z)-(R)-2-(Benzhydrylidene-amino)-4-((1S,5R,7R)-10,10-dimethyl-3,3-dioxo-3λ⁶-thia-4-aza-tricyclo[5.2.1.0^1,5]decane-4-carbonyl)-hex-2-enedioic acid 1-tert-butyl ester 6-ethyl ester

There total 3 articles about (Z)-(R)-2-(Benzhydrylidene-amino)-4-((1S,5R,7R)-10,10-dimethyl-3,3-dioxo-3λ⁶-thia-4-aza-tricyclo[5.2.1.0^1,5]decane-4-carbonyl)-hex-2-enedioic acid 1-tert-butyl ester 6-ethyl 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: 75.0%

ethyl bromoacetate (105-36-2) + (Z)-2-(Benzhydrylidene-amino)-5-((1S,5R,7R)-10,10-dimethyl-3,3-dioxo-3λ6-thia-4-aza-tricyclo[5.2.1.01,5]dec-4-yl)-5-oxo-pent-2-enoic acid tert-butyl ester (342376-58-3) → (Z)-(R)-2-(Benzhydrylidene-amino)-4-((1S,5R,7R)-10,10-dimethyl-3,3-dioxo-3λ6-thia-4-aza-tricyclo[5.2.1.01,5]decane-4-carbonyl)-hex-2-enedioic acid 1-tert-butyl ester 6-ethyl ester (342376-62-9)

Guidance literature:

With sodium hydroxide; N-benzyl-N,N,N-triethylammonium chloride; In acetonitrile; at 20 ℃; for 1h;

DOI:10.1016/S0040-4039(01)00147-2

Reference yield:

N-(diphenylmethylene)glycine tert-butyl ester (81477-94-3) → (Z)-(R)-2-(Benzhydrylidene-amino)-4-((1S,5R,7R)-10,10-dimethyl-3,3-dioxo-3λ6-thia-4-aza-tricyclo[5.2.1.01,5]decane-4-carbonyl)-hex-2-enedioic acid 1-tert-butyl ester 6-ethyl ester (342376-62-9)

Guidance literature:

Multi-step reaction with 3 steps

1: KOtBu / tetrahydrofuran / 0.5 h / -78 °C

2: 80 percent / Me₃Al / toluene / 48 h / 50 °C

3: 75 percent / NaOH; TEBA-Cl / acetonitrile / 1 h / 20 °C

With sodium hydroxide; potassium tert-butylate; N-benzyl-N,N,N-triethylammonium chloride; trimethylaluminum; In tetrahydrofuran; toluene; acetonitrile; 1: Michael addition/1,3-prototropic shift;

DOI:10.1016/S0040-4039(01)00147-2

Reference yield:

2-(benzhydrylidene-amino)-pent-2-enedioic acid 1-tert-butyl ester 5-methyl ester (434331-68-7) → (Z)-(R)-2-(Benzhydrylidene-amino)-4-((1S,5R,7R)-10,10-dimethyl-3,3-dioxo-3λ6-thia-4-aza-tricyclo[5.2.1.01,5]decane-4-carbonyl)-hex-2-enedioic acid 1-tert-butyl ester 6-ethyl ester (342376-62-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 80 percent / Me₃Al / toluene / 48 h / 50 °C

2: 75 percent / NaOH; TEBA-Cl / acetonitrile / 1 h / 20 °C

With sodium hydroxide; N-benzyl-N,N,N-triethylammonium chloride; trimethylaluminum; In toluene; acetonitrile;

DOI:10.1016/S0040-4039(01)00147-2

upstream raw materials:

ethyl bromoacetate

(Z)-2-(Benzhydrylidene-amino)-5-((1S,5R,7R)-10,10-dimethyl-3,3-dioxo-3λ⁶-thia-4-aza-tricyclo[5.2.1.0^1,5]dec-4-yl)-5-oxo-pent-2-enoic acid tert-butyl ester

N-(diphenylmethylene)glycine tert-butyl ester

2-(benzhydrylidene-amino)-pent-2-enedioic acid 1-tert-butyl ester 5-methyl ester

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