Water → HCID 178476468, compound

HRID 638322Notes

Reaction equation

HRID 638322 reaction equation
[C:1]([O:4][CH2:5][C:6]1[CH2:7][S:8][C@@H:9]2[C@H:22]([NH:23][C:24](=[O:57])/[C:25](=[N:51]\[O:52][CH2:53][CH:54]3[CH2:56][CH2:55]3)/[C:26]3[N:27]=[C:28]([NH:31]C(C4C=CC=CC=4)(C4C=CC=CC=4)C4C=CC=CC=4)[S:29][CH:30]=3)[C:21](=[O:58])[N:10]2[C:11]=1[C:12]([O:14][CH:15]([O:17][C:18](=[O:20])[CH3:19])[CH3:16])=[O:13])(=[O:3])[NH2:2].O>C(O)=O>[NH2:31][C:28]1[S:29][CH:30]=[C:26](/[C:25](=[N:51]/[O:52][CH2:53][CH:54]2[CH2:56][CH2:55]2)/[C:24]([NH:23][C@@H:22]2[C:21](=[O:58])[N:10]3[C:11]([C:12]([O:14][CH:15]([O:17][C:18](=[O:20])[CH3:19])[CH3:16])=[O:13])=[C:6]([CH2:5][O:4][C:1](=[O:3])[NH2:2])[CH2:7][S:8][C@H:9]23)=[O:57])[N:27]=1

Participants

4

Reactant 2

HCID 962WaterHCID 178476466HCID 178476466, compound

Product 1

HCID 178476468HCID 178476468, compoundYield 51%

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

1-Acetoxy-1-ethyl (6R,7R)-3-carbamoyloxymethyl-7-[(Z)-2-cyclopropylmethoxyimino-2-(2-tritylaminothiazol-4-yl)acetamido]ceph-3-em-4-carboxylate (1.5 g) was dissolved in formic acid (15 ml) and water (7.5 ml) was added. After 1.5 hour at 21°, the mixture was filtered and the filter-cake was leached with formic acid-water (2:1). The combined filtrates were concentrated and the residue was mixed with isopropanol when a solution formed. This was evaporated to dryness and the residue was partitioned between ethyl acetate and aqueous sodium bicarbonate solution. The aqueous layer was extracted with more ethyl acetate and the combined organic layers were washed with brine and dried with magnesium sulphate. After evaporation, the residue was triturated with isopropanol (5 ml) to give the title compound (540 mg); [α]D21 +17.9° (c 1.2, CHCl3); λmax (ethanol) 238.5 nm (E1 cm1% 287), λinfl 256 nm (E1 cm1% 249) and λinfl 280 nm (E1 cm1% 179).

Workup

  1. filtrationthe mixture was filtered
  2. concentrationThe combined filtrates were concentrated
  3. additionthe residue was mixed with isopropanol when a solution
  4. customformed
  5. customThis was evaporated to dryness
  6. customthe residue was partitioned between ethyl acetate and aqueous sodium bicarbonate solution
  7. extractionThe aqueous layer was extracted with more ethyl acetate
  8. washthe combined organic layers were washed with brine
  9. dry with materialdried with magnesium sulphate
  10. customAfter evaporation
  11. customthe residue was triturated with isopropanol (5 ml)

Sources & evidence

ORD record
ord-12e1c457e5f947febc2a21d964fa6b5b
Source dataset
uspto-grants-1985_12
Patent number
US04560683

Reaction notes

Loading…