(6R,7R)-3-[(Z)-3-(Morpholine-4-carbonyloxy)-propenyl]-8-oxo-7-{2-[2-(trityl-amino)-thiazol-4-yl]-2-[(Z)-trityloxyimino]-acetylamino}-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid 4-methoxy-benzyl ester

Base Information

• Chemical Name: (6R,7R)-3-[(Z)-3-(Morpholine-4-carbonyloxy)-propenyl]-8-oxo-7-{2-[2-(trityl-amino)-thiazol-4-yl]-2-[(Z)-trityloxyimino]-acetylamino}-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid 4-methoxy-benzyl ester
• CAS No.: 133731-63-2
• Molecular Formula: C₆₆H₅₈N₆O₉S₂
• Molecular Weight: 1143.35

Synonyms:

Chemical Property of (6R,7R)-3-[(Z)-3-(Morpholine-4-carbonyloxy)-propenyl]-8-oxo-7-{2-[2-(trityl-amino)-thiazol-4-yl]-2-[(Z)-trityloxyimino]-acetylamino}-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid 4-methoxy-benzyl ester

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Technology Process of (6R,7R)-3-[(Z)-3-(Morpholine-4-carbonyloxy)-propenyl]-8-oxo-7-{2-[2-(trityl-amino)-thiazol-4-yl]-2-[(Z)-trityloxyimino]-acetylamino}-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid 4-methoxy-benzyl ester

There total 7 articles about (6R,7R)-3-[(Z)-3-(Morpholine-4-carbonyloxy)-propenyl]-8-oxo-7-{2-[2-(trityl-amino)-thiazol-4-yl]-2-[(Z)-trityloxyimino]-acetylamino}-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid 4-methoxy-benzyl 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:

para-methoxybenzyl (6R,7R)-7-amino-3-chloromethyl-3-cephem-4-carboxylate hydrochloride → (6R,7R)-3-[(Z)-3-(Morpholine-4-carbonyloxy)-propenyl]-8-oxo-7-{2-[2-(trityl-amino)-thiazol-4-yl]-2-[(Z)-trityloxyimino]-acetylamino}-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid 4-methoxy-benzyl ester (133731-63-2)

Guidance literature:

Multi-step reaction with 4 steps

1: 1.) 1-hydroxybenzotriazole, DCC, 2.) Et₃N / 1.) DMF, 1 h, 2.) DMF, 18 h

2: NaI / acetone / 1 h

3: ethyl acetate / 4 h

4: 1.) 1M NaOH / 1.) CH₂Cl₂, H₂O, 2.) CH₂Cl₂, r.t.

With sodium hydroxide; benzotriazol-1-ol; triethylamine; dicyclohexyl-carbodiimide; sodium iodide; In ethyl acetate; acetone;

DOI:10.7164/antibiotics.47.1526

Reference yield:

1,4-bis<(1-imidazolyl)carbonyloxy>-cis-2-butene (1026530-53-9) → (6R,7R)-3-[(Z)-3-(Morpholine-4-carbonyloxy)-propenyl]-8-oxo-7-{2-[2-(trityl-amino)-thiazol-4-yl]-2-[(Z)-trityloxyimino]-acetylamino}-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid 4-methoxy-benzyl ester (133731-63-2)

Guidance literature:

Multi-step reaction with 3 steps

1: tetrahydrofuran

2: 1.) ozone, 2.) Me₂S / 1.) MeOH, -78 deg C, 2.) MeOH, r.t.

3: 1.) 1M NaOH / 1.) CH₂Cl₂, H₂O, 2.) CH₂Cl₂, r.t.

With sodium hydroxide; dimethylsulfide; ozone; In tetrahydrofuran;

DOI:10.7164/antibiotics.47.1526

Reference yield:

4-methoxyphenylmethyl 7-<(Z)-2-(2-tritylaminothiazol-4-yl)-2-trityloxyiminoacetamido>-3-chloromethyl-3-cephem-4-carboxylate (134482-51-2) → (6R,7R)-3-[(Z)-3-(Morpholine-4-carbonyloxy)-propenyl]-8-oxo-7-{2-[2-(trityl-amino)-thiazol-4-yl]-2-[(Z)-trityloxyimino]-acetylamino}-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid 4-methoxy-benzyl ester (133731-63-2)

Guidance literature:

Multi-step reaction with 3 steps

1: NaI / acetone / 1 h

2: ethyl acetate / 4 h

3: 1.) 1M NaOH / 1.) CH₂Cl₂, H₂O, 2.) CH₂Cl₂, r.t.

With sodium hydroxide; sodium iodide; In ethyl acetate; acetone;

DOI:10.7164/antibiotics.47.1526

upstream raw materials:

1-morpholinylcarbonyloxyacetaldehyde

1,4-bis<(1-imidazolyl)carbonyloxy>-cis-2-butene

1,4-bis(1-morpholinylcarbonyloxy)-cis-2-butene

4-methoxyphenylmethyl 7-<(Z)-2-(2-tritylaminothiazol-4-yl)-2-trityloxyiminoacetamido>-3-chloromethyl-3-cephem-4-carboxylate

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