Triethylamine → 8-Oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

HRID 1973078Notes

Reaction equation

HRID 1973078 reaction equation
CC1N=C(SC[C:9]2[CH2:16][S:15][CH:14]3[N:11]([C:12](=[O:18])[CH:13]3N)[C:10]=2[C:19]([O:21]C(C2C=CC=CC=2)C2C=CC=CC=2)=[O:20])SN=1.C(N(CC)CC)C.S=C(SCC(O)=O)C>C(Cl)Cl>[O:18]=[C:12]1[N:11]2[CH:14]([S:15][CH2:16][CH:9]=[C:10]2[C:19]([OH:21])=[O:20])[CH2:13]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 192946Thioacetylthioglycolic acidHCID 14477596HCID 14477596, compound

Product 1

HCID 190919938-Oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

0.01 mol. of 7-[D-2-amino-2-(2-thienyl)acetamido]-3-[[(3-methyl-1,2,4-thiadiazol-5-yl)thio]methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid, trifluoroacetate salt (prepared by the procedure of Example 7, but substituting 3-[[(3-methyl-1,2,4-thiadiazol-5-yl)thio]methyl]-7-amino- 8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid, diphenylmethyl ester in part b) is brought into solution with triethylamine in methylene chloride and 0.015 mol. of [(1-thioxoethyl)thio]acetic acid (prepared as described in U.S. Pat. No. 3,341,518) is added. The reaction mixture is permitted to stand for three hours and worked up according to the procedure of Example 7 to obtain 7-[D-2-[(2-thienyl)-2-[(1-thioxoethyl)amino]acetyl]amino]-3-[[3-methyl-1,2,4-thiadiazol-5-yl)thio]methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]-oct-2-ene-2-carboxylic acid.

Workup

  1. addition3,341,518) is added

Sources & evidence

ORD record
ord-9037922f8cf64c14808774eb408fdfc1
Source dataset
uspto-grants-1976_12
Patent number
US03996219

Reaction notes

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