(6R)-7t-((R)-2-tert-butoxycarbonylamino-2-phenyl-acetylamino)-3-(5-methyl-[1,3,4]thiadiazol-2-ylsulfanylmethyl)-5ξ,8-dioxo-(6rH)-5λ⁴-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid acetoxymethyl ester

Base Information

• Chemical Name: (6R)-7t-((R)-2-tert-butoxycarbonylamino-2-phenyl-acetylamino)-3-(5-methyl-[1,3,4]thiadiazol-2-ylsulfanylmethyl)-5ξ,8-dioxo-(6rH)-5λ⁴-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid acetoxymethyl ester
• CAS No.: 63491-69-0
• Molecular Formula: C₂₇H₃₁N₅O₉S₃
• Molecular Weight: 665.769

Synonyms:(6R)-7t-((R)-2-tert-butoxycarbonylamino-2-phenyl-acetylamino)-3-(5-methyl-[1,3,4]thiadiazol-2-ylsulfanylmethyl)-5ξ,8-dioxo-(6rH)-5λ⁴-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid acetoxymethyl ester

Chemical Property of (6R)-7t-((R)-2-tert-butoxycarbonylamino-2-phenyl-acetylamino)-3-(5-methyl-[1,3,4]thiadiazol-2-ylsulfanylmethyl)-5ξ,8-dioxo-(6rH)-5λ⁴-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid acetoxymethyl ester

Chemical Property:

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Technology Process of (6R)-7t-((R)-2-tert-butoxycarbonylamino-2-phenyl-acetylamino)-3-(5-methyl-[1,3,4]thiadiazol-2-ylsulfanylmethyl)-5ξ,8-dioxo-(6rH)-5λ⁴-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid acetoxymethyl ester

There total 5 articles about (6R)-7t-((R)-2-tert-butoxycarbonylamino-2-phenyl-acetylamino)-3-(5-methyl-[1,3,4]thiadiazol-2-ylsulfanylmethyl)-5ξ,8-dioxo-(6rH)-5λ⁴-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid acetoxymethyl 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:

2-(tert-butoxycarbonylamino)-2-phenylacetic acid (2900-27-8,3601-66-9,14675-97-9,33125-05-2) → (6R)-7t-((R)-2-tert-butoxycarbonylamino-2-phenyl-acetylamino)-3-(5-methyl-[1,3,4]thiadiazol-2-ylsulfanylmethyl)-5ξ,8-dioxo-(6rH)-5λ4-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid acetoxymethyl ester (63491-69-0)

Guidance literature:

Multi-step reaction with 2 steps

1: (i) monotrimethylsilylacetamide, THF, (ii) /BRN= 529873/, ClCO₂iBu

2: (i) /BRN= 1740473/, iPr₂NEt, (ii) MCPBA

DOI:10.1021/jm00219a009

Reference yield:

(6R,7R)-7-amino-3-(5-methyl-1,3,4-thiadiazol-2-ylthiomethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid (30246-33-4) → (6R)-7t-((R)-2-tert-butoxycarbonylamino-2-phenyl-acetylamino)-3-(5-methyl-[1,3,4]thiadiazol-2-ylsulfanylmethyl)-5ξ,8-dioxo-(6rH)-5λ4-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid acetoxymethyl ester (63491-69-0)

Guidance literature:

Multi-step reaction with 2 steps

1: (i) monotrimethylsilylacetamide, THF, (ii) /BRN= 529873/, ClCO₂iBu

2: (i) /BRN= 1740473/, iPr₂NEt, (ii) MCPBA

DOI:10.1021/jm00219a009

Reference yield:

(6R)-7t-((R)-2-tert-butoxycarbonylamino-2-phenyl-acetylamino)-3-(5-methyl-[1,3,4]thiadiazol-2-ylsulfanylmethyl)-8-oxo-(6rH)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid (139975-06-7) → (6R)-7t-((R)-2-tert-butoxycarbonylamino-2-phenyl-acetylamino)-3-(5-methyl-[1,3,4]thiadiazol-2-ylsulfanylmethyl)-5ξ,8-dioxo-(6rH)-5λ4-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid acetoxymethyl ester (63491-69-0)

Guidance literature:

Multi-step reaction with 2 steps

1: MCPBA / CHCl₃ / 0 °C

2: iPr₂NEt / acetone / Ambient temperature

With N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; In chloroform; acetone;

DOI:10.1021/jm00219a009

upstream raw materials:

acetoxymethyl bromide

(6R)-7t-((R)-2-tert-butoxycarbonylamino-2-phenyl-acetylamino)-3-(5-methyl-[1,3,4]thiadiazol-2-ylsulfanylmethyl)-8-oxo-(6rH)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid

(6R)-7t-((R)-2-tert-butoxycarbonylamino-2-phenyl-acetylamino)-3-(5-methyl-[1,3,4]thiadiazol-2-ylsulfanylmethyl)-5ξ,8-dioxo-(6rH)-5λ⁴-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid

2-(tert-butoxycarbonylamino)-2-phenylacetic acid

Downstream raw materials:

(6R)-7t-((R)-2-tert-butoxycarbonylamino-2-phenyl-acetylamino)-3-(5-methyl-[1,3,4]thiadiazol-2-ylsulfanylmethyl)-8-oxo-(6rH)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid acetoxymethyl ester

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