Hydrochloric Acid → HCID 88501806, compound

HRID 467381Notes

Reaction equation

HRID 467381 reaction equation
[CH3:1][C:2]1[O:7][C:6](=[O:8])[CH:5]=[C:4]([S:9][CH2:10][C:11]2[CH2:12][S:13][C@@H:14]3[C@H:34]([NH:35][C:36](=[O:84])/[C:37](/[C:59]4[N:60]=[C:61]([NH:64]C(C5C=CC=CC=5)(C5C=CC=CC=5)C5C=CC=CC=5)[S:62][CH:63]=4)=[N:38]\[O:39]C(C4C=CC=CC=4)(C4C=CC=CC=4)C4C=CC=CC=4)[C:33](=[O:85])[N:15]3[C:16]=2[C:17]([O:19]C(C2C=CC=CC=2)C2C=CC=CC=2)=[O:18])[CH:3]=1.Cl.O.[K+].[Br-]>C(O)=O>[NH2:64][C:61]1[S:62][CH:63]=[C:59](/[C:37](=[N:38]/[OH:39])/[C:36]([NH:35][C@@H:34]2[C:33](=[O:85])[N:15]3[C:16]([C:17]([OH:19])=[O:18])=[C:11]([CH2:10][S:9][C:4]4[CH:3]=[C:2]([CH3:1])[O:7][C:6](=[O:8])[CH:5]=4)[CH2:12][S:13][C@H:14]23)=[O:84])[N:60]=1

Participants

6

Reactant 4

HCID 313Hydrochloric Acid2×HCID 962WaterHCID 253877Potassium BromideHCID 178429664HCID 178429664, compound

Product 1

HCID 88501806HCID 88501806, compound

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

Diphenylmethyl 3-(6-methyl-2-oxo-2H-pyran-4-ylthiomethyl)-7β-[2-(2-tritylaminothiazol-4-yl)-2-(Z)-trityloxyiminoacetamido]ceph-3-em-4-carboxylate (969 mg) was dissolved in 100% formic acid (14.9 ml) and 1N hydrochloric acid (0.825 ml) and water (0.825 ml) were added. The mixture was stirred at room temperature for 0.5 h and then concentrated hydrochloric acid (0.66 ml) was added. The mixture was stirred for 1 h and then the solid was filtered off and washed with 90% formic acid. The combined filtrates were evaporated and a 1:1 mixture of toluene and tetrahydrofuran was evaporated from the residue twice. The residue was triturated with ether and the solid filtered off and washed with ether. The solid was suspended in water and the pH adjusted to 2.6 with 0.1N sodium hydroxide solution. The resulting solid was filtered off, washed with water and dried under vacuum to give the product. υmax (KBr) 1773, 1675 and 1624cm-1 ; δ[(CD3)2SO] 2.16 (3H, s), 3.47 (1H, d, J 17.9Hz), 3.70 (1H, d, J 18.0Hz), 4.11 (1H, d, J 12.9Hz), 4.19 (1H, d, J 13.1Hz), 5.18 (1H, d, J 4.8Hz), 5.79 (1H, dd, J 4.8 and 8.2Hz), 6.00 (1H, s), 6.21 (1H, s), 6.66 (1H, s), 7.17 (2H, s), 9.48 (1H, s).

Workup

  1. stirringThe mixture was stirred for 1 h
  2. filtrationthe solid was filtered off
  3. washwashed with 90% formic acid
  4. customThe combined filtrates were evaporated
  5. additiona 1:1 mixture of toluene and tetrahydrofuran
  6. customwas evaporated from the residue twice
  7. customThe residue was triturated with ether
  8. filtrationthe solid filtered off
  9. washwashed with ether
  10. filtrationThe resulting solid was filtered off
  11. washwashed with water
  12. customdried under vacuum
  13. customto give the product

Sources & evidence

ORD record
ord-990856528f24482f80958d3bdacc237f
Source dataset
uspto-grants-1992_10
Patent number
US05158946

Reaction notes

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