HCID 141579559, compound → HCID 88321529, compound

HRID 6292Notes

Reaction equation

HRID 6292 reaction equation
[O:1]=[C:2]1[CH2:6][CH2:5][C@@H:4]([C:7]2[CH2:8][S:9][C@@H:10]3[C@H:21]([NH:22][C:23](=[O:71])/[C:24](/[C:46]4[N:47]=[C:48]([NH:51]C(C5C=CC=CC=5)(C5C=CC=CC=5)C5C=CC=CC=5)[S:49][CH:50]=4)=[N:25]\[O:26]C(C4C=CC=CC=4)(C4C=CC=CC=4)C4C=CC=CC=4)[C:20](=[O:72])[N:11]3[C:12]=2[C:13]([O:15]C(C)(C)C)=[O:14])[O:3]1>Cl.C(O)=O>[NH2:51][C:48]1[S:49][CH:50]=[C:46](/[C:24](=[N:25]/[OH:26])/[C:23]([NH:22][C@@H:21]2[C:20](=[O:72])[N:11]3[C:12]([C:13]([OH:15])=[O:14])=[C:7]([CH:4]4[O:3][C:2](=[O:1])[CH2:6][CH2:5]4)[CH2:8][S:9][C@H:10]23)=[O:71])[N:47]=1

Participants

4

Reactant 1

HCID 141579559HCID 141579559, compound

Product 1

HCID 88321529HCID 88321529, compound

Reagents, catalysts & solvents 2

HCID 284Formic AcidSolventHCID 313Hydrochloric AcidSolvent2×

Procedure

t-Butyl (6R,7R)-3-[(5S)-2-oxotetrahydrofuran-5-yl]-7-[2-(2-tritylaminothiazol-4-yl)-2-(Z)-trityloxyiminoacetamido]ceph-3-em-4-carboxylate (0.22 g) was dissolved in 0.1M hydrochloric acid in 90% formic acid (2.5 ml) and stirred for 1 h. Concentrated hydrochloric acid (0.1 ml) was added and stirring was continued for a further 0.5 h. The precipitate was filtered off, washed with 90% formic acid, and the filtrate was evaporated to dryness. The residue in water was adjusted to pH3 with solid potassium carbonate, washed with ether and freeze dried. The crude product (0.153 g) was chromatographed on HP20SS, eluting with 0,2,4,6% THF in water. Fractions containing the title compound were combined, concentrated and freeze dried (41 mg, 40%), νmax (KBr) 1764, 1664, 1609, 1529, 1389 and 1184 cm-1 ; δH (D2O) 2.1-2.8 (4H,m , 3.37 and 3.63, 3.39 and 3.53 (2H,2ABq,J17.5,17.8 Hz), 5.21, 5.23 (1H,2d, J4.6 Hz), 5.5-5.65 (1H,m), 5.82 (1H,d,J4.6 Hz), 6.95 (1H,s); [mass spectrum: + ve ion (thioglyerol) MH+, 454].

Workup

  1. stirringstirring
  2. waitwas continued for a further 0.5 h
  3. filtrationThe precipitate was filtered off
  4. washwashed with 90% formic acid
  5. customthe filtrate was evaporated to dryness
  6. washwashed with ether and freeze
  7. customdried
  8. customThe crude product (0.153 g) was chromatographed on HP20SS
  9. washeluting with 0,2,4,6% THF in water
  10. additionFractions containing the title compound
  11. concentrationconcentrated
  12. dry with materialfreeze dried (41 mg, 40%), νmax (KBr) 1764, 1664, 1609, 1529, 1389 and 1184 cm-1

Sources & evidence

ORD record
ord-42452324fa004ae9a61634f23f042346
Source dataset
uspto-grants-1993_09
Patent number
US05246926

Reaction notes

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