Product Name

  • Name

    7-MAC

  • EINECS 611-404-7
  • CAS No. 56610-72-1
  • Article Data11
  • CAS DataBase
  • Density 1.5 g/cm3
  • Solubility
  • Melting Point 120°C(lit.)
  • Formula C24H24N6O4S2
  • Boiling Point 743.2 °C at 760 mmHg
  • Molecular Weight 524.624
  • Flash Point 403.2 °C
  • Transport Information
  • Appearance faint yellow to yellow powder
  • Safety
  • Risk Codes
  • Molecular Structure Molecular Structure of 56610-72-1 (7-MAC)
  • Hazard Symbols
  • Synonyms 5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylicacid, 7-amino-7-methoxy-3-[[(1-methyl-1H-tetrazol-5-yl)thio]methyl]-8-oxo-,diphenylmethyl ester, (6R-cis)-;Diphenylmethyl 7b-amino-7a-methoxy-3-[[(1-methyl-1H-tetrazol-5-yl)thio]methyl]-3-cephem-4-carboxylate;
  • PSA 176.06000
  • LogP 2.74380

Synthetic route

C31H28N6O5S2

C31H28N6O5S2

diphenylmethyl (6R,7S)-7-amino-7-methoxy-3-<<(1-methyl-1H-tetrazol-5-yl)thio>methyl>-Δ3-cephem-4-carboxylate
56610-72-1

diphenylmethyl (6R,7S)-7-amino-7-methoxy-3-<<(1-methyl-1H-tetrazol-5-yl)thio>methyl>-Δ3-cephem-4-carboxylate

Conditions
ConditionsYield
With pyridine; bis(trichloromethyl) carbonate In dichloromethane at -25 - 5℃; for 3h; Reagent/catalyst; Temperature; Solvent; Inert atmosphere;94.1%
(6R-cis)-7-methoxy-3-<<(1-methyl-1-H-tetrazol-5-yl)thio>methyl>-8-oxo<(phenylacetyl)amino>-5-thia-1-azabicyclo<4.2.0>oct-2-ene-2-carboxylic acid diphenylmethyl ester
64278-77-9

(6R-cis)-7-methoxy-3-<<(1-methyl-1-H-tetrazol-5-yl)thio>methyl>-8-oxo<(phenylacetyl)amino>-5-thia-1-azabicyclo<4.2.0>oct-2-ene-2-carboxylic acid diphenylmethyl ester

diphenylmethyl (6R,7S)-7-amino-7-methoxy-3-<<(1-methyl-1H-tetrazol-5-yl)thio>methyl>-Δ3-cephem-4-carboxylate
56610-72-1

diphenylmethyl (6R,7S)-7-amino-7-methoxy-3-<<(1-methyl-1H-tetrazol-5-yl)thio>methyl>-Δ3-cephem-4-carboxylate

Conditions
ConditionsYield
With pyridine; phosphorus pentachloride In methanol; dichloromethane at -30 - 5℃; for 4h; Reagent/catalyst;91%
Stage #1: (6R-cis)-7-methoxy-3-<<(1-methyl-1-H-tetrazol-5-yl)thio>methyl>-8-oxo<(phenylacetyl)amino>-5-thia-1-azabicyclo<4.2.0>oct-2-ene-2-carboxylic acid diphenylmethyl ester With pyridine; phosphorus pentachloride In dichloromethane at 5 - 8℃; for 2h;
Stage #2: In methanol at -30 - -10℃; for 2h;		90%
2-amino-benzenethiol
137-07-5

2-amino-benzenethiol

(6R,7S)-7-[1-Chloro-but-(E)-ylideneamino]-7-methoxy-3-(1-methyl-1H-tetrazol-5-ylsulfanylmethyl)-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester
75072-10-5

(6R,7S)-7-[1-Chloro-but-(E)-ylideneamino]-7-methoxy-3-(1-methyl-1H-tetrazol-5-ylsulfanylmethyl)-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester

A

2-propylbenzo[d]thiazole
17229-76-4

2-propylbenzo[d]thiazole

B

diphenylmethyl (6R,7S)-7-amino-7-methoxy-3-<<(1-methyl-1H-tetrazol-5-yl)thio>methyl>-Δ3-cephem-4-carboxylate
56610-72-1

diphenylmethyl (6R,7S)-7-amino-7-methoxy-3-<<(1-methyl-1H-tetrazol-5-yl)thio>methyl>-Δ3-cephem-4-carboxylate

C

(6R,7S)-7-Butyrylamino-7-methoxy-3-(1-methyl-1H-tetrazol-5-ylsulfanylmethyl)-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester
75072-09-2

(6R,7S)-7-Butyrylamino-7-methoxy-3-(1-methyl-1H-tetrazol-5-ylsulfanylmethyl)-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester

Conditions
ConditionsYield
With pyridine In dichloromethane for 1.5h; Ambient temperature;A 45%
B 15%
C 23%
...Expand
(6R,7S)-7-[1-Chloro-but-(E)-ylideneamino]-7-methoxy-3-(1-methyl-1H-tetrazol-5-ylsulfanylmethyl)-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester
75072-10-5

(6R,7S)-7-[1-Chloro-but-(E)-ylideneamino]-7-methoxy-3-(1-methyl-1H-tetrazol-5-ylsulfanylmethyl)-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester

A

2-propylbenzo[d]thiazole
17229-76-4

2-propylbenzo[d]thiazole

B

diphenylmethyl (6R,7S)-7-amino-7-methoxy-3-<<(1-methyl-1H-tetrazol-5-yl)thio>methyl>-Δ3-cephem-4-carboxylate
56610-72-1

diphenylmethyl (6R,7S)-7-amino-7-methoxy-3-<<(1-methyl-1H-tetrazol-5-yl)thio>methyl>-Δ3-cephem-4-carboxylate

C

(6R,7S)-7-Butyrylamino-7-methoxy-3-(1-methyl-1H-tetrazol-5-ylsulfanylmethyl)-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester
75072-09-2

(6R,7S)-7-Butyrylamino-7-methoxy-3-(1-methyl-1H-tetrazol-5-ylsulfanylmethyl)-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester

Conditions
ConditionsYield
With pyridine; 2-amino-benzenethiol In dichloromethane for 1.5h; Ambient temperature;A 45%
B 15%
C 23%
...Expand
2-amino-benzenethiol
137-07-5

2-amino-benzenethiol

(6R,7S)-7-[5-Benzhydryloxycarbonyl-5-tert-butoxycarbonylamino-1-chloro-pent-(Z)-ylideneamino]-7-methoxy-3-(1-methyl-1H-tetrazol-5-ylsulfanylmethyl)-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester

(6R,7S)-7-[5-Benzhydryloxycarbonyl-5-tert-butoxycarbonylamino-1-chloro-pent-(Z)-ylideneamino]-7-methoxy-3-(1-methyl-1H-tetrazol-5-ylsulfanylmethyl)-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester

A

diphenylmethyl (6R,7S)-7-amino-7-methoxy-3-<<(1-methyl-1H-tetrazol-5-yl)thio>methyl>-Δ3-cephem-4-carboxylate
56610-72-1

diphenylmethyl (6R,7S)-7-amino-7-methoxy-3-<<(1-methyl-1H-tetrazol-5-yl)thio>methyl>-Δ3-cephem-4-carboxylate

B

5-Benzothiazol-2-yl-2-tert-butoxycarbonylamino-pentanoic acid benzhydryl ester

5-Benzothiazol-2-yl-2-tert-butoxycarbonylamino-pentanoic acid benzhydryl ester

Conditions
ConditionsYield
With pyridine In dichloromethane Ambient temperature;A 25%
B 35%
...Expand
(6R,7S)-7-[5-Benzhydryloxycarbonyl-5-tert-butoxycarbonylamino-1-chloro-pent-(Z)-ylideneamino]-7-methoxy-3-(1-methyl-1H-tetrazol-5-ylsulfanylmethyl)-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester

(6R,7S)-7-[5-Benzhydryloxycarbonyl-5-tert-butoxycarbonylamino-1-chloro-pent-(Z)-ylideneamino]-7-methoxy-3-(1-methyl-1H-tetrazol-5-ylsulfanylmethyl)-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester

A

diphenylmethyl (6R,7S)-7-amino-7-methoxy-3-<<(1-methyl-1H-tetrazol-5-yl)thio>methyl>-Δ3-cephem-4-carboxylate
56610-72-1

diphenylmethyl (6R,7S)-7-amino-7-methoxy-3-<<(1-methyl-1H-tetrazol-5-yl)thio>methyl>-Δ3-cephem-4-carboxylate

B

5-Benzothiazol-2-yl-2-tert-butoxycarbonylamino-pentanoic acid benzhydryl ester

5-Benzothiazol-2-yl-2-tert-butoxycarbonylamino-pentanoic acid benzhydryl ester

Conditions
ConditionsYield
With pyridine; 2-amino-benzenethiol In dichloromethane Ambient temperature;A 25%
B 35%
(6R)-7t-(3,5-di-tert-butyl-4-hydroxy-benzylideneamino)-7c-methoxy-3-(1-methyl-1H-tetrazol-5-ylsulfanylmethyl)-8-oxo-(6rH)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester
56023-19-9

(6R)-7t-(3,5-di-tert-butyl-4-hydroxy-benzylideneamino)-7c-methoxy-3-(1-methyl-1H-tetrazol-5-ylsulfanylmethyl)-8-oxo-(6rH)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester

diphenylmethyl (6R,7S)-7-amino-7-methoxy-3-<<(1-methyl-1H-tetrazol-5-yl)thio>methyl>-Δ3-cephem-4-carboxylate
56610-72-1

diphenylmethyl (6R,7S)-7-amino-7-methoxy-3-<<(1-methyl-1H-tetrazol-5-yl)thio>methyl>-Δ3-cephem-4-carboxylate

Conditions
ConditionsYield
With girard's reagent T In methanol; ethyl acetate Ambient temperature;
(6R,7S)-7-(5-Benzhydryloxycarbonyl-5-tert-butoxycarbonylamino-pentanoylamino)-7-methoxy-3-(1-methyl-1H-tetrazol-5-ylsulfanylmethyl)-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester
57793-21-2

(6R,7S)-7-(5-Benzhydryloxycarbonyl-5-tert-butoxycarbonylamino-pentanoylamino)-7-methoxy-3-(1-methyl-1H-tetrazol-5-ylsulfanylmethyl)-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester

diphenylmethyl (6R,7S)-7-amino-7-methoxy-3-<<(1-methyl-1H-tetrazol-5-yl)thio>methyl>-Δ3-cephem-4-carboxylate
56610-72-1

diphenylmethyl (6R,7S)-7-amino-7-methoxy-3-<<(1-methyl-1H-tetrazol-5-yl)thio>methyl>-Δ3-cephem-4-carboxylate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: phosgene-pyridine / CH2Cl2 / Ambient temperature
2: 25 percent / pyridine / CH2Cl2 / Ambient temperature
View Scheme
Multi-step reaction with 2 steps
1: phosgene-pyridine / CH2Cl2 / Ambient temperature
2: 25 percent / pyridine, o-amino-benzenethiol / CH2Cl2 / Ambient temperature
View Scheme
(6R,7S)-7-Butyrylamino-7-methoxy-3-(1-methyl-1H-tetrazol-5-ylsulfanylmethyl)-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester
75072-09-2

(6R,7S)-7-Butyrylamino-7-methoxy-3-(1-methyl-1H-tetrazol-5-ylsulfanylmethyl)-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester

diphenylmethyl (6R,7S)-7-amino-7-methoxy-3-<<(1-methyl-1H-tetrazol-5-yl)thio>methyl>-Δ3-cephem-4-carboxylate
56610-72-1

diphenylmethyl (6R,7S)-7-amino-7-methoxy-3-<<(1-methyl-1H-tetrazol-5-yl)thio>methyl>-Δ3-cephem-4-carboxylate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: phosgene-pyridine / CH2Cl2 / 3 h / Ambient temperature
2: 15 percent / pyridine, o-amino-benzenethiol / CH2Cl2 / 1.5 h / Ambient temperature
View Scheme
7β-amino-3-<<(1-methyl-1H-tetrazol-5-yl)thio>methyl>ceph-3-em-4-oic acid benzhydryl ester
53090-86-1

7β-amino-3-<<(1-methyl-1H-tetrazol-5-yl)thio>methyl>ceph-3-em-4-oic acid benzhydryl ester

diphenylmethyl (6R,7S)-7-amino-7-methoxy-3-<<(1-methyl-1H-tetrazol-5-yl)thio>methyl>-Δ3-cephem-4-carboxylate
56610-72-1

diphenylmethyl (6R,7S)-7-amino-7-methoxy-3-<<(1-methyl-1H-tetrazol-5-yl)thio>methyl>-Δ3-cephem-4-carboxylate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: (i) benzene, (ii) PbO2, 1,2-dichloroethane, (iii) /BRN= 1098229/, benzene
2: Girard T / ethyl acetate; methanol / Ambient temperature
View Scheme
7-Aminocephalosporanic acid
957-68-6

7-Aminocephalosporanic acid

diphenylmethyl (6R,7S)-7-amino-7-methoxy-3-<<(1-methyl-1H-tetrazol-5-yl)thio>methyl>-Δ3-cephem-4-carboxylate
56610-72-1

diphenylmethyl (6R,7S)-7-amino-7-methoxy-3-<<(1-methyl-1H-tetrazol-5-yl)thio>methyl>-Δ3-cephem-4-carboxylate

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1.1: boron trifluoride diethyl etherate / acetonitrile / 2.5 h / 50 °C
2.1: sodium hydrogencarbonate / water; acetone / 3.67 h / 0 - 20 °C
3.1: dicyclohexyl-carbodiimide; dmap / dichloromethane / -20 °C
4.1: 3-chloro-benzenecarboperoxoic acid / chloroform / 6 h / 0 °C
5.1: phosphorus trichloride / dichloromethane / 3 h / Reflux
6.1: tert-butylhypochlorite / tetrahydrofuran; methanol / 0.37 h / -78 °C / Inert atmosphere
7.1: pyridine; phosphorus pentachloride / dichloromethane / 2 h / 5 - 8 °C
7.2: 2 h / -30 - -10 °C
View Scheme
Multi-step reaction with 7 steps
1: boron trifluoride diethyl etherate / acetonitrile / 2.5 h / 50 °C
2: sodium hydrogencarbonate / acetone; water / 3 h / 0 - 25 °C
3: dicyclohexyl-carbodiimide; dmap / dichloromethane / -20 °C
4: 3-chloro-benzenecarboperoxoic acid / chloroform / 6 h / 0 - 5 °C
5: phosphorus trichloride / dichloromethane / 3 h / Reflux
6: tert-butylhypochlorite; lithium methanolate / tetrahydrofuran / 0.33 h / -78 °C / Inert atmosphere
7: pyridine; phosphorus pentachloride / dichloromethane; methanol / 4 h / -30 - 5 °C
View Scheme
(6R,7R)-7-amino-3-[(1H-1-methyltetrazol-5-yl)thio]methylceph-3-em-4-carboxylic acid
24209-38-9

(6R,7R)-7-amino-3-[(1H-1-methyltetrazol-5-yl)thio]methylceph-3-em-4-carboxylic acid

diphenylmethyl (6R,7S)-7-amino-7-methoxy-3-<<(1-methyl-1H-tetrazol-5-yl)thio>methyl>-Δ3-cephem-4-carboxylate
56610-72-1

diphenylmethyl (6R,7S)-7-amino-7-methoxy-3-<<(1-methyl-1H-tetrazol-5-yl)thio>methyl>-Δ3-cephem-4-carboxylate

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1.1: sodium hydrogencarbonate / water; acetone / 3.67 h / 0 - 20 °C
2.1: dicyclohexyl-carbodiimide; dmap / dichloromethane / -20 °C
3.1: 3-chloro-benzenecarboperoxoic acid / chloroform / 6 h / 0 °C
4.1: phosphorus trichloride / dichloromethane / 3 h / Reflux
5.1: tert-butylhypochlorite / tetrahydrofuran; methanol / 0.37 h / -78 °C / Inert atmosphere
6.1: pyridine; phosphorus pentachloride / dichloromethane / 2 h / 5 - 8 °C
6.2: 2 h / -30 - -10 °C
View Scheme
Multi-step reaction with 6 steps
1: sodium hydrogencarbonate / acetone; water / 3 h / 0 - 25 °C
2: dicyclohexyl-carbodiimide; dmap / dichloromethane / -20 °C
3: 3-chloro-benzenecarboperoxoic acid / chloroform / 6 h / 0 - 5 °C
4: phosphorus trichloride / dichloromethane / 3 h / Reflux
5: tert-butylhypochlorite; lithium methanolate / tetrahydrofuran / 0.33 h / -78 °C / Inert atmosphere
6: pyridine; phosphorus pentachloride / dichloromethane; methanol / 4 h / -30 - 5 °C
View Scheme
(6R,7R)-3-((1-methyl-1H-tetrazol-5-ylthio)methyl)-8-oxo-7-(2-phenylacetamido)-5-thia-1-aza-bicyclo [4.2.0]oct-2-ene-2-carboxylic acid
47653-82-7

(6R,7R)-3-((1-methyl-1H-tetrazol-5-ylthio)methyl)-8-oxo-7-(2-phenylacetamido)-5-thia-1-aza-bicyclo [4.2.0]oct-2-ene-2-carboxylic acid

diphenylmethyl (6R,7S)-7-amino-7-methoxy-3-<<(1-methyl-1H-tetrazol-5-yl)thio>methyl>-Δ3-cephem-4-carboxylate
56610-72-1

diphenylmethyl (6R,7S)-7-amino-7-methoxy-3-<<(1-methyl-1H-tetrazol-5-yl)thio>methyl>-Δ3-cephem-4-carboxylate

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: dicyclohexyl-carbodiimide; dmap / dichloromethane / -20 °C
2.1: 3-chloro-benzenecarboperoxoic acid / chloroform / 6 h / 0 °C
3.1: phosphorus trichloride / dichloromethane / 3 h / Reflux
4.1: tert-butylhypochlorite / tetrahydrofuran; methanol / 0.37 h / -78 °C / Inert atmosphere
5.1: pyridine; phosphorus pentachloride / dichloromethane / 2 h / 5 - 8 °C
5.2: 2 h / -30 - -10 °C
View Scheme
Multi-step reaction with 5 steps
1: dicyclohexyl-carbodiimide; dmap / dichloromethane / -20 °C
2: 3-chloro-benzenecarboperoxoic acid / chloroform / 6 h / 0 - 5 °C
3: phosphorus trichloride / dichloromethane / 3 h / Reflux
4: tert-butylhypochlorite; lithium methanolate / tetrahydrofuran / 0.33 h / -78 °C / Inert atmosphere
5: pyridine; phosphorus pentachloride / dichloromethane; methanol / 4 h / -30 - 5 °C
View Scheme
(6R,7R)-benzhydryl-3-((1-methyl-1H-tetrazol-5-ylthio)methyl)-8-oxo-7-(2-phenylacetamido)-5-thia-1-azabicyclo[4.2.0]oct-3-ene-2-carboxylic

(6R,7R)-benzhydryl-3-((1-methyl-1H-tetrazol-5-ylthio)methyl)-8-oxo-7-(2-phenylacetamido)-5-thia-1-azabicyclo[4.2.0]oct-3-ene-2-carboxylic

diphenylmethyl (6R,7S)-7-amino-7-methoxy-3-<<(1-methyl-1H-tetrazol-5-yl)thio>methyl>-Δ3-cephem-4-carboxylate
56610-72-1

diphenylmethyl (6R,7S)-7-amino-7-methoxy-3-<<(1-methyl-1H-tetrazol-5-yl)thio>methyl>-Δ3-cephem-4-carboxylate

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: 3-chloro-benzenecarboperoxoic acid / chloroform / 6 h / 0 °C
2.1: phosphorus trichloride / dichloromethane / 3 h / Reflux
3.1: tert-butylhypochlorite / tetrahydrofuran; methanol / 0.37 h / -78 °C / Inert atmosphere
4.1: pyridine; phosphorus pentachloride / dichloromethane / 2 h / 5 - 8 °C
4.2: 2 h / -30 - -10 °C
View Scheme
Multi-step reaction with 4 steps
1: 3-chloro-benzenecarboperoxoic acid / chloroform / 6 h / 0 - 5 °C
2: phosphorus trichloride / dichloromethane / 3 h / Reflux
3: tert-butylhypochlorite; lithium methanolate / tetrahydrofuran / 0.33 h / -78 °C / Inert atmosphere
4: pyridine; phosphorus pentachloride / dichloromethane; methanol / 4 h / -30 - 5 °C
View Scheme
C31H28N6O5S2
68474-81-7

C31H28N6O5S2

diphenylmethyl (6R,7S)-7-amino-7-methoxy-3-<<(1-methyl-1H-tetrazol-5-yl)thio>methyl>-Δ3-cephem-4-carboxylate
56610-72-1

diphenylmethyl (6R,7S)-7-amino-7-methoxy-3-<<(1-methyl-1H-tetrazol-5-yl)thio>methyl>-Δ3-cephem-4-carboxylate

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: phosphorus trichloride / dichloromethane / 3 h / Reflux
2.1: tert-butylhypochlorite / tetrahydrofuran; methanol / 0.37 h / -78 °C / Inert atmosphere
3.1: pyridine; phosphorus pentachloride / dichloromethane / 2 h / 5 - 8 °C
3.2: 2 h / -30 - -10 °C
View Scheme
Multi-step reaction with 3 steps
1: phosphorus trichloride / dichloromethane / 3 h / Reflux
2: tert-butylhypochlorite; lithium methanolate / tetrahydrofuran / 0.33 h / -78 °C / Inert atmosphere
3: pyridine; phosphorus pentachloride / dichloromethane; methanol / 4 h / -30 - 5 °C
View Scheme
diphenylmethyl (6R,7S)-7-amino-7-methoxy-3-<<(1-methyl-1H-tetrazol-5-yl)thio>methyl>-Δ3-cephem-4-carboxylate
56610-72-1

diphenylmethyl (6R,7S)-7-amino-7-methoxy-3-<<(1-methyl-1H-tetrazol-5-yl)thio>methyl>-Δ3-cephem-4-carboxylate

Glyoxilic acid
298-12-4

Glyoxilic acid

C26H24N6O6S2

C26H24N6O6S2

Conditions
ConditionsYield
Stage #1: Glyoxilic acid With 1,1'-carbonyldiimidazole In dichloromethane
Stage #2: diphenylmethyl (6R,7S)-7-amino-7-methoxy-3-<<(1-methyl-1H-tetrazol-5-yl)thio>methyl>-Δ3-cephem-4-carboxylate In dichloromethane at 40℃; for 10h; Reagent/catalyst;		98.8%
2,2-dimercaptoacetic acid

2,2-dimercaptoacetic acid

diphenylmethyl (6R,7S)-7-amino-7-methoxy-3-<<(1-methyl-1H-tetrazol-5-yl)thio>methyl>-Δ3-cephem-4-carboxylate
56610-72-1

diphenylmethyl (6R,7S)-7-amino-7-methoxy-3-<<(1-methyl-1H-tetrazol-5-yl)thio>methyl>-Δ3-cephem-4-carboxylate

C26H26N6O5S4

C26H26N6O5S4

Conditions
ConditionsYield
With 1,1'-carbonyldiimidazole In ethyl acetate at 40℃; for 10h;98.6%
chlorocarbonyl-[4-(4-methoxy-benzyloxy)-phenyl]-acetic acid 4-methoxy-benzyl ester
64952-86-9

chlorocarbonyl-[4-(4-methoxy-benzyloxy)-phenyl]-acetic acid 4-methoxy-benzyl ester

diphenylmethyl (6R,7S)-7-amino-7-methoxy-3-<<(1-methyl-1H-tetrazol-5-yl)thio>methyl>-Δ3-cephem-4-carboxylate
56610-72-1

diphenylmethyl (6R,7S)-7-amino-7-methoxy-3-<<(1-methyl-1H-tetrazol-5-yl)thio>methyl>-Δ3-cephem-4-carboxylate

(6R,7S)-7-Methoxy-7-{2-(4-methoxy-benzyloxycarbonyl)-2-[4-(4-methoxy-benzyloxy)-phenyl]-acetylamino}-3-(1-methyl-1H-tetrazol-5-ylsulfanylmethyl)-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester
66216-32-8

(6R,7S)-7-Methoxy-7-{2-(4-methoxy-benzyloxycarbonyl)-2-[4-(4-methoxy-benzyloxy)-phenyl]-acetylamino}-3-(1-methyl-1H-tetrazol-5-ylsulfanylmethyl)-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester

Conditions
ConditionsYield
With pyridine75%
2-[(3S)-(4-ethyl-2,3-dioxo-1-piperazinyl)carboxamido]-3-formyloxybutyryl chloride

2-[(3S)-(4-ethyl-2,3-dioxo-1-piperazinyl)carboxamido]-3-formyloxybutyryl chloride

diphenylmethyl (6R,7S)-7-amino-7-methoxy-3-<<(1-methyl-1H-tetrazol-5-yl)thio>methyl>-Δ3-cephem-4-carboxylate
56610-72-1

diphenylmethyl (6R,7S)-7-amino-7-methoxy-3-<<(1-methyl-1H-tetrazol-5-yl)thio>methyl>-Δ3-cephem-4-carboxylate

(6R,7S)-7-[[(3S)-2-[(4-ethyl-2,3-dioxo-1-piperazinyl)carboxamido]-3-formyloxy-1-oxobutyl]amino]-7-methoxy-3-[(1-methyl-1H-tetrazol-5-yl)thiomethyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid diphenylmethyl ester

(6R,7S)-7-[[(3S)-2-[(4-ethyl-2,3-dioxo-1-piperazinyl)carboxamido]-3-formyloxy-1-oxobutyl]amino]-7-methoxy-3-[(1-methyl-1H-tetrazol-5-yl)thiomethyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid diphenylmethyl ester

Conditions
ConditionsYield
With triethylamine In dichloromethane at -10℃;51.5%
gloutaric dichloride
2873-74-7

gloutaric dichloride

diphenylmethyl (6R,7S)-7-amino-7-methoxy-3-<<(1-methyl-1H-tetrazol-5-yl)thio>methyl>-Δ3-cephem-4-carboxylate
56610-72-1

diphenylmethyl (6R,7S)-7-amino-7-methoxy-3-<<(1-methyl-1H-tetrazol-5-yl)thio>methyl>-Δ3-cephem-4-carboxylate

C29H30N6O7S2

C29H30N6O7S2

Conditions
ConditionsYield
With pyridine In dichloromethane Cooling with ice;17%
L-α-[[[(4-methoxyphenyl)-methoxy]carbonyl]amino]-2-thiopheneacetic acid
59966-06-2

L-α-[[[(4-methoxyphenyl)-methoxy]carbonyl]amino]-2-thiopheneacetic acid

diphenylmethyl (6R,7S)-7-amino-7-methoxy-3-<<(1-methyl-1H-tetrazol-5-yl)thio>methyl>-Δ3-cephem-4-carboxylate
56610-72-1

diphenylmethyl (6R,7S)-7-amino-7-methoxy-3-<<(1-methyl-1H-tetrazol-5-yl)thio>methyl>-Δ3-cephem-4-carboxylate

(6R)-7c-methoxy-7t-[(Ξ)-2-(4-methoxy-benzyloxycarbonylamino)-2-thiophen-2-yl-acetylamino]-3-(1-methyl-1H-tetrazol-5-ylsulfanylmethyl)-8-oxo-(6rH)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester
64044-40-2

(6R)-7c-methoxy-7t-[(Ξ)-2-(4-methoxy-benzyloxycarbonylamino)-2-thiophen-2-yl-acetylamino]-3-(1-methyl-1H-tetrazol-5-ylsulfanylmethyl)-8-oxo-(6rH)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester

Conditions
ConditionsYield
(i) diisopropylethylamine, isobutyl chloroformate, CH2Cl2, (ii) /BRN= 5406406/; Multistep reaction;
cyanomethylmercapto acetyl chloride
52069-55-3

cyanomethylmercapto acetyl chloride

diphenylmethyl (6R,7S)-7-amino-7-methoxy-3-<<(1-methyl-1H-tetrazol-5-yl)thio>methyl>-Δ3-cephem-4-carboxylate
56610-72-1

diphenylmethyl (6R,7S)-7-amino-7-methoxy-3-<<(1-methyl-1H-tetrazol-5-yl)thio>methyl>-Δ3-cephem-4-carboxylate

Cefmetazole
56796-20-4, 82263-66-9

Cefmetazole

Conditions
ConditionsYield
(i) PhNEt2, 1,2-dichloroethane, (ii) CF3CO2H, anisole; Multistep reaction;
(1-methyl-4-nitro-1H-imidazol-2-ylsulfanyl)-acetyl chloride

(1-methyl-4-nitro-1H-imidazol-2-ylsulfanyl)-acetyl chloride

diphenylmethyl (6R,7S)-7-amino-7-methoxy-3-<<(1-methyl-1H-tetrazol-5-yl)thio>methyl>-Δ3-cephem-4-carboxylate
56610-72-1

diphenylmethyl (6R,7S)-7-amino-7-methoxy-3-<<(1-methyl-1H-tetrazol-5-yl)thio>methyl>-Δ3-cephem-4-carboxylate

(6R)-7c-methoxy-7t-[2-(1-methyl-4-nitro-1H-imidazol-2-ylsulfanyl)-acetylamino]-3-(1-methyl-1H-tetrazol-5-ylsulfanylmethyl)-8-oxo-(6rH)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid
72193-33-0

(6R)-7c-methoxy-7t-[2-(1-methyl-4-nitro-1H-imidazol-2-ylsulfanyl)-acetylamino]-3-(1-methyl-1H-tetrazol-5-ylsulfanylmethyl)-8-oxo-(6rH)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid

Conditions
ConditionsYield
(i) PhNEt2, 1,2-dichloro-ethane, (ii) CF3CO2H, anisole; Multistep reaction;
(3-methyl-5-nitro-3H-imidazol-4-ylsulfanyl)-acetyl chloride
72193-39-6

(3-methyl-5-nitro-3H-imidazol-4-ylsulfanyl)-acetyl chloride

diphenylmethyl (6R,7S)-7-amino-7-methoxy-3-<<(1-methyl-1H-tetrazol-5-yl)thio>methyl>-Δ3-cephem-4-carboxylate
56610-72-1

diphenylmethyl (6R,7S)-7-amino-7-methoxy-3-<<(1-methyl-1H-tetrazol-5-yl)thio>methyl>-Δ3-cephem-4-carboxylate

(6R)-7c-methoxy-7t-[2-(3-methyl-5-nitro-3H-imidazol-4-ylsulfanyl)-acetylamino]-3-(1-methyl-1H-tetrazol-5-ylsulfanylmethyl)-8-oxo-(6rH)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid
72193-31-8

(6R)-7c-methoxy-7t-[2-(3-methyl-5-nitro-3H-imidazol-4-ylsulfanyl)-acetylamino]-3-(1-methyl-1H-tetrazol-5-ylsulfanylmethyl)-8-oxo-(6rH)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid

Conditions
ConditionsYield
(i) PhNEt2, 1,2-dichloro-ethane, (ii) CF3CO2H, anisole; Multistep reaction;
(1-methyl-5-nitro-1H-imidazol-2-ylsulfanyl)-acetyl chloride

(1-methyl-5-nitro-1H-imidazol-2-ylsulfanyl)-acetyl chloride

diphenylmethyl (6R,7S)-7-amino-7-methoxy-3-<<(1-methyl-1H-tetrazol-5-yl)thio>methyl>-Δ3-cephem-4-carboxylate
56610-72-1

diphenylmethyl (6R,7S)-7-amino-7-methoxy-3-<<(1-methyl-1H-tetrazol-5-yl)thio>methyl>-Δ3-cephem-4-carboxylate

(6R)-7c-methoxy-7t-[2-(1-methyl-5-nitro-1H-imidazol-2-ylsulfanyl)-acetylamino]-3-(1-methyl-1H-tetrazol-5-ylsulfanylmethyl)-8-oxo-(6rH)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid
72193-34-1

(6R)-7c-methoxy-7t-[2-(1-methyl-5-nitro-1H-imidazol-2-ylsulfanyl)-acetylamino]-3-(1-methyl-1H-tetrazol-5-ylsulfanylmethyl)-8-oxo-(6rH)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid

Conditions
ConditionsYield
(i) PhNEt2, 1,2-dichloro-ethane, (ii) CF3CO2H, anisole; Multistep reaction;
(1-methyl-5-nitro-1H-imidazol-4-ylsulfanyl)-acetyl chloride

(1-methyl-5-nitro-1H-imidazol-4-ylsulfanyl)-acetyl chloride

diphenylmethyl (6R,7S)-7-amino-7-methoxy-3-<<(1-methyl-1H-tetrazol-5-yl)thio>methyl>-Δ3-cephem-4-carboxylate
56610-72-1

diphenylmethyl (6R,7S)-7-amino-7-methoxy-3-<<(1-methyl-1H-tetrazol-5-yl)thio>methyl>-Δ3-cephem-4-carboxylate

(6R)-7c-methoxy-7t-[2-(1-methyl-5-nitro-1H-imidazol-4-ylsulfanyl)-acetylamino]-3-(1-methyl-1H-tetrazol-5-ylsulfanylmethyl)-8-oxo-(6rH)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid
72193-32-9

(6R)-7c-methoxy-7t-[2-(1-methyl-5-nitro-1H-imidazol-4-ylsulfanyl)-acetylamino]-3-(1-methyl-1H-tetrazol-5-ylsulfanylmethyl)-8-oxo-(6rH)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid

Conditions
ConditionsYield
(i) PhNEt2, 1,2-dichloro-ethane, (ii) CF3CO2H, anisole; Multistep reaction;
(R)-2-amino-4-thiophen-2-yl-4H-oxazol-5-one; hydrochloride
67645-41-4

(R)-2-amino-4-thiophen-2-yl-4H-oxazol-5-one; hydrochloride

diphenylmethyl (6R,7S)-7-amino-7-methoxy-3-<<(1-methyl-1H-tetrazol-5-yl)thio>methyl>-Δ3-cephem-4-carboxylate
56610-72-1

diphenylmethyl (6R,7S)-7-amino-7-methoxy-3-<<(1-methyl-1H-tetrazol-5-yl)thio>methyl>-Δ3-cephem-4-carboxylate

(6R)-7c-methoxy-3-(1-methyl-1H-tetrazol-5-ylsulfanylmethyl)-8-oxo-7t-((R)-2-thiophen-2-yl-2-ureido-acetylamino)-(6rH)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester
67780-07-8

(6R)-7c-methoxy-3-(1-methyl-1H-tetrazol-5-ylsulfanylmethyl)-8-oxo-7t-((R)-2-thiophen-2-yl-2-ureido-acetylamino)-(6rH)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester

Conditions
ConditionsYield
With methyloxirane In dichloromethane; N,N-dimethyl-formamide
(S)-2-amino-4-thiophen-2-yl-4H-oxazol-5-one; hydrochloride
67645-39-0

(S)-2-amino-4-thiophen-2-yl-4H-oxazol-5-one; hydrochloride

diphenylmethyl (6R,7S)-7-amino-7-methoxy-3-<<(1-methyl-1H-tetrazol-5-yl)thio>methyl>-Δ3-cephem-4-carboxylate
56610-72-1

diphenylmethyl (6R,7S)-7-amino-7-methoxy-3-<<(1-methyl-1H-tetrazol-5-yl)thio>methyl>-Δ3-cephem-4-carboxylate

(6R)-7c-methoxy-3-(1-methyl-1H-tetrazol-5-ylsulfanylmethyl)-8-oxo-7t-((S)-2-thiophen-2-yl-2-ureido-acetylamino)-(6rH)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester
65642-60-6

(6R)-7c-methoxy-3-(1-methyl-1H-tetrazol-5-ylsulfanylmethyl)-8-oxo-7t-((S)-2-thiophen-2-yl-2-ureido-acetylamino)-(6rH)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester

Conditions
ConditionsYield
With methyloxirane In dichloromethane; N,N-dimethyl-formamide
diphenylmethyl (6R,7S)-7-amino-7-methoxy-3-<<(1-methyl-1H-tetrazol-5-yl)thio>methyl>-Δ3-cephem-4-carboxylate
56610-72-1

diphenylmethyl (6R,7S)-7-amino-7-methoxy-3-<<(1-methyl-1H-tetrazol-5-yl)thio>methyl>-Δ3-cephem-4-carboxylate

Carbonic acid benzyl ester 4-chlorocarbonylmethyl-phenyl ester
86862-84-2

Carbonic acid benzyl ester 4-chlorocarbonylmethyl-phenyl ester

(6R,7S)-7-[2-(4-Benzyloxycarbonyloxy-phenyl)-acetylamino]-7-methoxy-3-(1-methyl-1H-tetrazol-5-ylsulfanylmethyl)-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester
86862-87-5

(6R,7S)-7-[2-(4-Benzyloxycarbonyloxy-phenyl)-acetylamino]-7-methoxy-3-(1-methyl-1H-tetrazol-5-ylsulfanylmethyl)-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester

Conditions
ConditionsYield
With pyridine In dichloromethane at 0℃; for 0.5h; Yield given;
diphenylmethyl (6R,7S)-7-amino-7-methoxy-3-<<(1-methyl-1H-tetrazol-5-yl)thio>methyl>-Δ3-cephem-4-carboxylate
56610-72-1

diphenylmethyl (6R,7S)-7-amino-7-methoxy-3-<<(1-methyl-1H-tetrazol-5-yl)thio>methyl>-Δ3-cephem-4-carboxylate

(6R,7R)-7-[2-Carboxy-2-(4-hydroxy-phenyl)-acetylamino]-6-methoxy-3-(1-methyl-1H-tetrazol-5-ylsulfanylmethyl)-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid

(6R,7R)-7-[2-Carboxy-2-(4-hydroxy-phenyl)-acetylamino]-6-methoxy-3-(1-methyl-1H-tetrazol-5-ylsulfanylmethyl)-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 75 percent / pyridine
2: 100 percent / AlCl3, anisole / 0.5 h / 0 °C
View Scheme
diphenylmethyl (6R,7S)-7-amino-7-methoxy-3-<<(1-methyl-1H-tetrazol-5-yl)thio>methyl>-Δ3-cephem-4-carboxylate
56610-72-1

diphenylmethyl (6R,7S)-7-amino-7-methoxy-3-<<(1-methyl-1H-tetrazol-5-yl)thio>methyl>-Δ3-cephem-4-carboxylate

(6R)-7t-((Ξ)-2-amino-2-thiophen-3-yl-acetylamino)-7c-methoxy-3-(1-methyl-1H-tetrazol-5-ylsulfanylmethyl)-8-oxo-(6rH)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid

(6R)-7t-((Ξ)-2-amino-2-thiophen-3-yl-acetylamino)-7c-methoxy-3-(1-methyl-1H-tetrazol-5-ylsulfanylmethyl)-8-oxo-(6rH)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: (i) diisopropylethylamine, isobutyl chloroformate, CH2Cl2, (ii) /BRN= 5406406/
2: CF3CO2H, anisole
View Scheme
diphenylmethyl (6R,7S)-7-amino-7-methoxy-3-<<(1-methyl-1H-tetrazol-5-yl)thio>methyl>-Δ3-cephem-4-carboxylate
56610-72-1

diphenylmethyl (6R,7S)-7-amino-7-methoxy-3-<<(1-methyl-1H-tetrazol-5-yl)thio>methyl>-Δ3-cephem-4-carboxylate

(6R)-7c-methoxy-3-(1-methyl-1H-tetrazol-5-ylsulfanylmethyl)-8-oxo-7t-((S)-2-thiophen-2-yl-2-ureido-acetylamino)-(6rH)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid
65700-47-2

(6R)-7c-methoxy-3-(1-methyl-1H-tetrazol-5-ylsulfanylmethyl)-8-oxo-7t-((S)-2-thiophen-2-yl-2-ureido-acetylamino)-(6rH)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: propyleneoxide / CH2Cl2; dimethylformamide
2: CF3CO2H, anisole / CH2Cl2
View Scheme
diphenylmethyl (6R,7S)-7-amino-7-methoxy-3-<<(1-methyl-1H-tetrazol-5-yl)thio>methyl>-Δ3-cephem-4-carboxylate
56610-72-1

diphenylmethyl (6R,7S)-7-amino-7-methoxy-3-<<(1-methyl-1H-tetrazol-5-yl)thio>methyl>-Δ3-cephem-4-carboxylate

(6R)-7c-methoxy-3-(1-methyl-1H-tetrazol-5-ylsulfanylmethyl)-8-oxo-7t-((R)-2-thiophen-2-yl-2-ureido-acetylamino)-(6rH)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid
74378-97-5

(6R)-7c-methoxy-3-(1-methyl-1H-tetrazol-5-ylsulfanylmethyl)-8-oxo-7t-((R)-2-thiophen-2-yl-2-ureido-acetylamino)-(6rH)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: propyleneoxide / CH2Cl2; dimethylformamide
2: CF3CO2H, anisole / CH2Cl2
View Scheme
diphenylmethyl (6R,7S)-7-amino-7-methoxy-3-<<(1-methyl-1H-tetrazol-5-yl)thio>methyl>-Δ3-cephem-4-carboxylate
56610-72-1

diphenylmethyl (6R,7S)-7-amino-7-methoxy-3-<<(1-methyl-1H-tetrazol-5-yl)thio>methyl>-Δ3-cephem-4-carboxylate

2-Bromoacetyl bromide
598-21-0

2-Bromoacetyl bromide

7-bromoacetamide-7-methoxy-3-(1-methyl-1H-5-tetrazolyl)thiomethyl-3-cephem-4-carboxylic acid diphenyl methyl ester
70035-75-5

7-bromoacetamide-7-methoxy-3-(1-methyl-1H-5-tetrazolyl)thiomethyl-3-cephem-4-carboxylic acid diphenyl methyl ester

Conditions
ConditionsYield
Stage #1: diphenylmethyl (6R,7S)-7-amino-7-methoxy-3-<<(1-methyl-1H-tetrazol-5-yl)thio>methyl>-Δ3-cephem-4-carboxylate; 2-Bromoacetyl bromide With pyridine In dichloromethane at -30 - -20℃; for 1h;
Stage #2: With N-Bromosuccinimide In methanol; dichloromethane at 0 - 5℃; for 1h;
With N,N-dimethyl-aniline In ethyl acetate at -5 - 0℃;
methanol
67-56-1

methanol

(6R-cis)-7-amino-3-<<(1-methyl-1H-tetrazol-5-yl)thio>methyl>-7-(methylthio)-8-oxo-5-thia-1-azabicyclo<4.2.0>oct-2-ene-2-carboxylic acid diphenylmethyl ester
67366-04-5

(6R-cis)-7-amino-3-<<(1-methyl-1H-tetrazol-5-yl)thio>methyl>-7-(methylthio)-8-oxo-5-thia-1-azabicyclo<4.2.0>oct-2-ene-2-carboxylic acid diphenylmethyl ester

diphenylmethyl (6R,7S)-7-amino-7-methoxy-3-<<(1-methyl-1H-tetrazol-5-yl)thio>methyl>-Δ3-cephem-4-carboxylate
56610-72-1

diphenylmethyl (6R,7S)-7-amino-7-methoxy-3-<<(1-methyl-1H-tetrazol-5-yl)thio>methyl>-Δ3-cephem-4-carboxylate

2-Bromoacetyl bromide
598-21-0

2-Bromoacetyl bromide

7-bromoacetamide-7-methoxy-3-(1-methyl-1H-5-tetrazolyl)thiomethyl-3-cephem-4-carboxylic acid diphenyl methyl ester
70035-75-5

7-bromoacetamide-7-methoxy-3-(1-methyl-1H-5-tetrazolyl)thiomethyl-3-cephem-4-carboxylic acid diphenyl methyl ester

Conditions
ConditionsYield
Stage #1: (6R-cis)-7-amino-3-<<(1-methyl-1H-tetrazol-5-yl)thio>methyl>-7-(methylthio)-8-oxo-5-thia-1-azabicyclo<4.2.0>oct-2-ene-2-carboxylic acid diphenylmethyl ester; diphenylmethyl (6R,7S)-7-amino-7-methoxy-3-<<(1-methyl-1H-tetrazol-5-yl)thio>methyl>-Δ3-cephem-4-carboxylate; 2-Bromoacetyl bromide With pyridine In dichloromethane at -30 - -20℃; for 1h;
Stage #2: In dichloromethane; water at 0 - 5℃;
Stage #3: methanol With N-Bromosuccinimide; sodium thiosulfate Purification / work up; more than 3 stages;
...Expand

7-MAC Specification

The 7-MAC, with the cas registry number 56610-72-1, has the systematic name of diphenylmethyl (6R,7S)-7-amino-7-methoxy-3-{[(1-methyl-1H-tetrazol-5-yl)sulfanyl]methyl}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate. This is a kind of faint yellow to yellow powder and is usually applied as the pharmaceutic intermediate, such as being the stem nucleus of some medicine as cefmetazole sodium, cefotetan.

The characteristics of this chemical are as follows: (1)ACD/LogP: 3.31; (2)# of Rule of 5 Violations: 2; (3)ACD/LogD (pH 5.5): 3.31; (4)ACD/LogD (pH 7.4): 3.31; (5)#H bond acceptors: 10; (6)#H bond donors: 2; (7)#Freely Rotating Bonds: 10; (8)Polar Surface Area: 176.06; (9)Index of Refraction: 1.733; (10)Molar Refractivity: 139.66 cm3; (11)Molar Volume: 348.5 cm3; (12)Polarizability: 55.36 ×10-24 cm3; (13)Surface Tension: 65.1 dyne/cm; (14)Density: 1.5 g/cm3; (15)Flash Point: 403.2 °C; (16)Enthalpy of Vaporization: 108.37 kJ/mol; (17)Boiling Point: 743.2 °C at 760 mmHg; (18)Vapour Pressure: 5.89E-22 mmHg at 25°C.

Additionally, you could convert the following datas into the molecular structure:
(1)SMILES:Cn1c(nnn1)SCC2=C(N3C(C(C3=O)(N)OC)SC2)C(=O)OC(c4ccccc4)c5ccccc5
(2)InChI:InChI=1/C24H24N6O4S2/c1-29-23(26-27-28-29)36-14-17-13-35-22-24(25,33-2)21(32)30(22)18(17)20(31)34-19(15-9-5-3-6-10-15)16-11-7-4-8-12-16/h3-12,19,22H,13-14,25H2,1-2H3/t22-,24+/m1/s1
(3)InChIKey:QGXKMJVEULWQSB-VWNXMTODBW

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