HCID 21426452, compound → HCID 21426436, compound

HRID 258698Notes

Reaction equation

HRID 258698 reaction equation
[C:1]([O:4][CH2:5][C:6]1[CH2:13][S:12][CH:11]2[N:8]([C:9](=[O:27])[CH:10]2[NH:14][C:15](=[O:26])[CH2:16][N:17]2[CH:21]=[CH:20][N:19]=[C:18]2[S:22]([CH3:25])(=[O:24])=[O:23])[C:7]=1[C:28]([O:30]C(C)(C)C)=[O:29])(=[O:3])[CH3:2]>FC(F)(F)C(O)=O>[C:1]([O:4][CH2:5][C:6]1[CH2:13][S:12][CH:11]2[N:8]([C:9](=[O:27])[CH:10]2[NH:14][C:15](=[O:26])[CH2:16][N:17]2[CH:21]=[CH:20][N:19]=[C:18]2[S:22]([CH3:25])(=[O:24])=[O:23])[C:7]=1[C:28]([OH:30])=[O:29])(=[O:3])[CH3:2]

Participants

3

Reactant 1

HCID 21426452HCID 21426452, compound

Product 1

HCID 21426436HCID 21426436, compoundYield 74.8%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

3-Acetoxymethyl-2-(tertiary butoxycarbonyl)-7-[(2-mesyl-imidazol-1-yl)-acetamido]-8-oxo-5-thia-1-aza-bicyclo[4,2,0]oct-2-ene (6 g.) is dissolved in trifluoroacetic acid (60 cc.). The reagents are contacted for 3 hours while keeping the temperature at about 4° C. The mixture is then concentrated to dryness under reduced pressure (1 mm.Hg) at 40° C., and the residue is recrystallised from acetonitrile (15 cc.) to give 3-acetoxymethyl-2-carboxy-7-[(2-mesyl-imidazol-1-yl)-acetamido]-8-oxo-5-thia-1-aza-bicyclo[4,2,0]oct-2-ene (4 g.), m.p. 223° C., [α]D20 = 78.9° ± 1.5° (c= 1, dimethylformamide).

Workup

  1. customat about 4° C
  2. concentrationThe mixture is then concentrated to dryness under reduced pressure (1 mm.Hg) at 40° C.
  3. customthe residue is recrystallised from acetonitrile (15 cc.)

Sources & evidence

ORD record
ord-d361be0ecd3244699a81af5797e24b01
Source dataset
uspto-grants-1977_07
Patent number
US04034088

Reaction notes

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