Benzyl 7-<(Z)-2-(Methoxyimino)-2-phenylacetamido>-1-oxa-2-oxocephem-4-carboxylate

Base Information

Chemical Name:Benzyl 7-<(Z)-2-(Methoxyimino)-2-phenylacetamido>-1-oxa-2-oxocephem-4-carboxylate
CAS No.:74281-12-2
Molecular Formula:C₂₃H₁₉N₃O₇
Molecular Weight:449.42
Hs Code.:

Synonyms:Benzyl 7-<(Z)-2-(Methoxyimino)-2-phenylacetamido>-1-oxa-2-oxocephem-4-carboxylate

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Chemical Property of Benzyl 7-<(Z)-2-(Methoxyimino)-2-phenylacetamido>-1-oxa-2-oxocephem-4-carboxylate

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Technology Process of Benzyl 7-<(Z)-2-(Methoxyimino)-2-phenylacetamido>-1-oxa-2-oxocephem-4-carboxylate

There total 17 articles about Benzyl 7-<(Z)-2-(Methoxyimino)-2-phenylacetamido>-1-oxa-2-oxocephem-4-carboxylate 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:

: 74280-93-6
1,2-secopenicillin tosylate

: 74281-12-2
Benzyl 7-<(Z)-2-(Methoxyimino)-2-phenylacetamido>-1-oxa-2-oxocephem-4-carboxylate

Guidance literature:: Multi-step reaction with 13 steps

1: 97 percent / Et₃N / CH₂Cl₂ / 1) -40 deg C, 30 min, 2) up to 0 deg C, 30 min.

2: 9.30 g / Cl₂ / CH₂Cl₂; CCl₄ / 1) -78 deg C, 30 min, 2) 0 deg C, 30 min

3: 7.59 g / Ag₂O, AgBF₄ / CH₂Cl₂ / 1) -30 deg C, 2) -20 deg C, 1.5h

4: 0.880 g / Pyridine / tetrahydrofuran / 1.5 h / -78 deg C -> room temp.

5: 0.730 g / camphorsulfonic acid, H₂O / CH₂Cl₂ / 0.58 h / Ambient temperature

6: 80 percent / O₃ / ethyl acetate / -78 °C

7: 1.49 g / Zn dust, propionic acid / CH₂Cl₂ / 0.5 h / 1) 0 deg C -> 13 deg C, 30 min, 2) 0 deg C after 30 min

8: 1.31 g / 2,6-Lutidine, SOCl₂ / CH₂Cl₂ / 1) -30 deg C -> 0 deg C , 20 min, 2) 0 deg C, 1.5h

9: 0.99 g / CH₂Cl₂ / 1) 12 h, room temperature, 2) 4.5 h heating

10: 75 percent / Zn dust, acetic acid / CH₂Cl₂ / 5 h / 15 °C

11: 85 percent / acetic anhydride / dimethylsulfoxide / 4 h / Ambient temperature

13: 1) DMF, POCl₃, 2) Pyridine

With pyridine; 2,6-dimethylpyridine; silver tetrafluoroborate; thionyl chloride; camphor-10-sulfonic acid; water; acetic anhydride; chlorine; ozone; acetic acid; propionic acid; triethylamine; N,N-dimethyl-formamide; silver(l) oxide; zinc; trichlorophosphate; In tetrahydrofuran; tetrachloromethane; dichloromethane; dimethyl sulfoxide; ethyl acetate;
DOI:10.1021/jo01306a028

Reference yield:

: 74310-18-2
7-<1-((Benzyloxy)carbonyl)-2-methylprop-1-enyl>-3-(hydroxymethyl)-2-oxa-4,7-diazabicyclo<3.2.0>hept-3-en-6-one

: 74281-12-2
Benzyl 7-<(Z)-2-(Methoxyimino)-2-phenylacetamido>-1-oxa-2-oxocephem-4-carboxylate

Guidance literature:: Multi-step reaction with 11 steps

1: 68 percent / Pyridine / CH₂Cl₂ / 1) -35 deg C -> 0 deg C, 1h, 2) 0 deg C, 1h

2: 0.880 g / Pyridine / tetrahydrofuran / 1.5 h / -78 deg C -> room temp.

3: 0.730 g / camphorsulfonic acid, H₂O / CH₂Cl₂ / 0.58 h / Ambient temperature

4: 80 percent / O₃ / ethyl acetate / -78 °C

5: 1.49 g / Zn dust, propionic acid / CH₂Cl₂ / 0.5 h / 1) 0 deg C -> 13 deg C, 30 min, 2) 0 deg C after 30 min

6: 1.31 g / 2,6-Lutidine, SOCl₂ / CH₂Cl₂ / 1) -30 deg C -> 0 deg C , 20 min, 2) 0 deg C, 1.5h

7: 0.99 g / CH₂Cl₂ / 1) 12 h, room temperature, 2) 4.5 h heating

8: 75 percent / Zn dust, acetic acid / CH₂Cl₂ / 5 h / 15 °C

9: 85 percent / acetic anhydride / dimethylsulfoxide / 4 h / Ambient temperature

11: 1) DMF, POCl₃, 2) Pyridine

With pyridine; 2,6-dimethylpyridine; thionyl chloride; camphor-10-sulfonic acid; water; acetic anhydride; ozone; acetic acid; propionic acid; N,N-dimethyl-formamide; zinc; trichlorophosphate; In tetrahydrofuran; dichloromethane; dimethyl sulfoxide; ethyl acetate;
DOI:10.1021/jo01306a028

Reference yield:

: 74280-98-1
3-(Acetoxymethyl)-7-<1-((benzyloxy)carbonyl)-2-methyl-prop-1-enyl>-2-oxa-4,7-diazabicyclo<3.2.0>hept-3-en-6-one

: 74281-12-2
Benzyl 7-<(Z)-2-(Methoxyimino)-2-phenylacetamido>-1-oxa-2-oxocephem-4-carboxylate

Guidance literature:: Multi-step reaction with 12 steps

1: 36 percent / K₂CO₃ / acetone; H₂O / 3 h / 55 °C

2: 68 percent / Pyridine / CH₂Cl₂ / 1) -35 deg C -> 0 deg C, 1h, 2) 0 deg C, 1h

3: 0.880 g / Pyridine / tetrahydrofuran / 1.5 h / -78 deg C -> room temp.

4: 0.730 g / camphorsulfonic acid, H₂O / CH₂Cl₂ / 0.58 h / Ambient temperature

5: 80 percent / O₃ / ethyl acetate / -78 °C

6: 1.49 g / Zn dust, propionic acid / CH₂Cl₂ / 0.5 h / 1) 0 deg C -> 13 deg C, 30 min, 2) 0 deg C after 30 min

7: 1.31 g / 2,6-Lutidine, SOCl₂ / CH₂Cl₂ / 1) -30 deg C -> 0 deg C , 20 min, 2) 0 deg C, 1.5h

8: 0.99 g / CH₂Cl₂ / 1) 12 h, room temperature, 2) 4.5 h heating

9: 75 percent / Zn dust, acetic acid / CH₂Cl₂ / 5 h / 15 °C

10: 85 percent / acetic anhydride / dimethylsulfoxide / 4 h / Ambient temperature

12: 1) DMF, POCl₃, 2) Pyridine

With pyridine; 2,6-dimethylpyridine; thionyl chloride; camphor-10-sulfonic acid; water; acetic anhydride; potassium carbonate; ozone; acetic acid; propionic acid; N,N-dimethyl-formamide; zinc; trichlorophosphate; In tetrahydrofuran; dichloromethane; water; dimethyl sulfoxide; ethyl acetate; acetone;
DOI:10.1021/jo01306a028