Acetic Acid → HCID 178460195, compound

HRID 329936Notes

Reaction equation

HRID 329936 reaction equation
[NH2:1][C:2]1[S:3][CH:4]=[C:5](/[C:7](=[N:25]/[O:26][C:27]([C:30]([OH:32])=[O:31])([CH3:29])[CH3:28])/[C:8]([NH:10][CH:11]2[C:23](=[O:24])[N:13]3[C:14]([C:20]([OH:22])=[O:21])=[C:15]([CH2:18][NH2:19])[CH2:16][S:17][C@H:12]23)=[O:9])[N:6]=1.[C:33]([C:35]1[C:36]([O:44]C(C2C=CC=CC=2)C2C=CC=CC=2)=[N:37][S:38][C:39]=1S(OC)=O)#[N:34].C(N(CC)CC)C.CC(O)=O>CN(C=O)C>[NH2:1][C:2]1[S:3][CH:4]=[C:5](/[C:7](=[N:25]/[O:26][C:27]([C:30]([OH:32])=[O:31])([CH3:29])[CH3:28])/[C:8]([NH:10][CH:11]2[C:23](=[O:24])[N:13]3[C:14]([C:20]([OH:22])=[O:21])=[C:15]([CH2:18][NH:19][C:39]4[S:38][N:37]=[C:36]([OH:44])[C:35]=4[C:33]#[N:34])[CH2:16][S:17][C@H:12]23)=[O:9])[N:6]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 8471TriethylamineHCID 19870396HCID 19870396, compoundHCID 88403825HCID 88403825, compound

Product 1

HCID 178460195HCID 178460195, compoundYield 61.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 7-[2-(2-aminothiazol-4-yl)-2-((Z)-1-carboxy-1-methylethoxyimino)acetamido]-3-aminomethylceph-3-em-4-carboxylic acid (900 mg) and methyl 4-cyano-3-diphenylmethoxyisothiazol-5-sulphinate (800 mg) in solution in DMF (15 ml) containing 1 ml triethylamine was stirred at ambient temperature for five hours. The mixture was neutralised with HOAc and evaporated. The residue was purified by HPLC eluting with a 70/30 v/v mixture of methanol and water, and then with methanol to yield 700 mg of the desired product, nmr in solvent A 1.5 (s, 6 H); 3.8-4.1 (m, 2 H); 4.1-4.3 (m, 2 H); 5.15 (d, 1 H); 5.85 (d, 1 H); 7.0 (s, 1 H); 7.2-7.6 (m, 10 H).

Workup

  1. customevaporated
  2. customThe residue was purified by HPLC
  3. washeluting with a 70/30 v/v mixture of methanol and water

Sources & evidence

ORD record
ord-42a96bac836045f9870c730d0ee2205f
Source dataset
uspto-grants-1990_01
Patent number
US04894371

Reaction notes

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