Trifluoroacetic acid → HCID 141560922, compound

HRID 1591267Notes

Reaction equation

HRID 1591267 reaction equation
[NH2:1][C:2]1[S:3][CH:4]=[C:5](/[C:7](=[N:43]/[O:44][CH3:45])/[C:8]([NH:10][CH:11]2[C:41](=[O:42])[N:13]3[C:14]([C:25]([O:27]C(C4C=CC=CC=4)C4C=CC=CC=4)=[O:26])=[C:15]([C:18]4[C:21](=[O:22])[C:20](=[O:23])[C:19]=4[CH3:24])[CH2:16][S:17][C@H:12]23)=[O:9])[N:6]=1.FC(F)(F)C(O)=O.C1(OC)C=CC=CC=1>>[NH2:1][C:2]1[S:3][CH:4]=[C:5](/[C:7](=[N:43]/[O:44][CH3:45])/[C:8]([NH:10][CH:11]2[C:41](=[O:42])[N:13]3[C:14]([C:25]([OH:27])=[O:26])=[C:15]([C:18]4[C:21](=[O:22])[C:20](=[O:23])[C:19]=4[CH3:24])[CH2:16][S:17][C@H:12]23)=[O:9])[N:6]=1

Participants

4

Reactant 3

HCID 6422Trifluoroacetic acid2×HCID 7519AnisoleHCID 141560924HCID 141560924, compound

Product 1

HCID 141560922HCID 141560922, compoundYield 86.5%

Procedure

Diphenylmethyl 7-[2-(2-aminothiazol-4-yl)-(Z)-2-methoxyiminoacetamido]-3-(3,4-dioxo-2-methyl-1-cyclobutenyl)-3-cephem-4-carboxylate (550 mg) was added to stirred and cooled (ice/H2O bath) trifluoroacetic acid (5 mL) containing anisole (1 mL). The cooling bath was removed, and stirring was continued for 0.66 hr at ambient temperatures. The solution was added to stirred diisopropyl ether to precipitate the trifluoroacetic acid salt of the title compound (353 mg, 70% yield) as a yellow powder.

Workup

  1. customThe cooling bath was removed
  2. stirringstirring
  3. additionThe solution was added
  4. stirringto stirred diisopropyl ether

Sources & evidence

ORD record
ord-ac84250e157f4140a230c23fae9760f0
Source dataset
uspto-grants-1993_04
Patent number
US05206360

Reaction notes

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