1-<((Benzyloxy)carbonyl)(triphenylphosphoranylidene)methyl>-3β-(phenoxyacetamido)-4β-<<<(trichloroethyl)carbonyl>oxy>acetoxy>azetidine-2-one

Base Information

Chemical Name:1-<((Benzyloxy)carbonyl)(triphenylphosphoranylidene)methyl>-3β-(phenoxyacetamido)-4β-<<<(trichloroethyl)carbonyl>oxy>acetoxy>azetidine-2-one
CAS No.:74281-09-7
Molecular Formula:C₄₃H₃₆Cl₃N₂O₁₀P
Molecular Weight:878.099
Hs Code.:

1-<((Benzyloxy)carbonyl)(triphenylphosphoranylidene)methyl>-3β-(phenoxyacetamido)-4β-<<<(trichloroethyl)carbonyl>oxy>acetoxy>azetidine-2-one

Synonyms:1-<((Benzyloxy)carbonyl)(triphenylphosphoranylidene)methyl>-3β-(phenoxyacetamido)-4β-<<<(trichloroethyl)carbonyl>oxy>acetoxy>azetidine-2-one

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Chemical Property of 1-<((Benzyloxy)carbonyl)(triphenylphosphoranylidene)methyl>-3β-(phenoxyacetamido)-4β-<<<(trichloroethyl)carbonyl>oxy>acetoxy>azetidine-2-one

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Technology Process of 1-<((Benzyloxy)carbonyl)(triphenylphosphoranylidene)methyl>-3β-(phenoxyacetamido)-4β-<<<(trichloroethyl)carbonyl>oxy>acetoxy>azetidine-2-one

There total 17 articles about 1-<((Benzyloxy)carbonyl)(triphenylphosphoranylidene)methyl>-3β-(phenoxyacetamido)-4β-<<<(trichloroethyl)carbonyl>oxy>acetoxy>azetidine-2-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:

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

: 74281-09-7
1-<((Benzyloxy)carbonyl)(triphenylphosphoranylidene)methyl>-3β-(phenoxyacetamido)-4β-<<<(trichloroethyl)carbonyl>oxy>acetoxy>azetidine-2-one

Guidance literature:: Multi-step reaction with 9 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

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

Reference yield:

: 73884-79-4
<<(Trichloroethoxy)carbonyl>oxy>acetyl Chloride

: 74281-09-7
1-<((Benzyloxy)carbonyl)(triphenylphosphoranylidene)methyl>-3β-(phenoxyacetamido)-4β-<<<(trichloroethyl)carbonyl>oxy>acetoxy>azetidine-2-one

Guidance literature:: Multi-step reaction with 9 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

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

Reference yield:

: 74231-21-3
<<(Trichloroethoxy)carbonyl>oxy>acetic acid

: 74281-09-7
1-<((Benzyloxy)carbonyl)(triphenylphosphoranylidene)methyl>-3β-(phenoxyacetamido)-4β-<<<(trichloroethyl)carbonyl>oxy>acetoxy>azetidine-2-one

Guidance literature:: Multi-step reaction with 10 steps

1: 84 percent / SOCl₂ / benzene / 2 h / Heating

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

3: 9.30 g / Cl₂ / CH₂Cl₂; CCl₄ / 1) -78 deg C, 30 min, 2) 0 deg C, 30 min

4: 7.59 g / Ag₂O, AgBF₄ / CH₂Cl₂ / 1) -30 deg C, 2) -20 deg C, 1.5h

5: 0.880 g / Pyridine / tetrahydrofuran / 1.5 h / -78 deg C -> room temp.

6: 0.730 g / camphorsulfonic acid, H₂O / CH₂Cl₂ / 0.58 h / Ambient temperature

7: 80 percent / O₃ / ethyl acetate / -78 °C

8: 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

9: 1.31 g / 2,6-Lutidine, SOCl₂ / CH₂Cl₂ / 1) -30 deg C -> 0 deg C , 20 min, 2) 0 deg C, 1.5h

10: 0.99 g / CH₂Cl₂ / 1) 12 h, room temperature, 2) 4.5 h heating

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