Hydrogen Peroxide → Diphenylmethyl (4R, 6R, 7R)-3-(1,4-dihydroxybut-1-yl)-7-phenylacetamidoceph-2-em-4-carboxylate

HRID 899492Notes

Reaction equation

HRID 899492 reaction equation
B.[O:2]1CCCC1.[OH:7][CH:8]([C:12]1[C@H:17]([C:18]([O:20][CH:21]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[O:19])[N:16]2[C:34](=[O:46])[C@@H:35]([NH:36][C:37](=[O:45])[CH2:38][C:39]3[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=3)[C@H:15]2[S:14][CH:13]=1)[CH2:9][CH:10]=[CH2:11].[OH-].[Na+].OO>O1CCCC1.C(OCC)(=O)C.O>[OH:7][CH:8]([C:12]1[C@H:17]([C:18]([O:20][CH:21]([C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=2)[C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[O:19])[N:16]2[C:34](=[O:46])[C@@H:35]([NH:36][C:37](=[O:45])[CH2:38][C:39]3[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=3)[C@H:15]2[S:14][CH:13]=1)[CH2:9][CH2:10][CH2:11][OH:2]

Participants

8

Reactant 4

HCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 2723981Borane;tetrahydrofuranHCID 131724666Diphenylmethyl (4R, 6R, 7R)-3(1-hydroxybut 3enyl)7phenylacetamidoceph-2em-4carboxylate

Product 1

HCID 131724667Diphenylmethyl (4R, 6R, 7R)-3-(1,4-dihydroxybut-1-yl)-7-phenylacetamidoceph-2-em-4-carboxylate

Reagents, catalysts & solvents 3

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

Borane-tetrahydrofuran complex (1M in tetrahydrofuran, 11.0 ml, 11.0 mmol) was added to diphenylmethyl (4R, 6R, 7R)-3-(1-hydroxybut-3-en-1-yl)-7-phenylacetamidoceph-2-em-4-carboxylate (S-diastereomer, 100 mg, 0.18 mmol) in tetrahydrofuran (2 ml) at 20° C. After 30 minutes water (1 ml) was added and the pH taken to within the range 7 to 8 with dilute aqueous sodium hydroxide. Hydrogen peroxide (30% in water, 0.15 ml, 1.35 mmol) was then added, and the pH maintained at 7 to 8 for 20 minutes, after which water and ethyl acetate were added. The organic layer was washed with brine, dried (MgSO4), and evaporated to give a residue which was purified by chromatography (50 to 100% ethyl acetate in hexane, silica gel) giving the S-diastereomer of the title compound identical to that obtained above (isomer P1), 35 mg (34%).

Workup

  1. temperaturethe pH maintained at 7 to 8 for 20 minutes
  2. washThe organic layer was washed with brine
  3. dry with materialdried (MgSO4)
  4. customevaporated
  5. customto give a residue which
  6. customwas purified by chromatography (50 to 100% ethyl acetate in hexane, silica gel)

Sources & evidence

ORD record
ord-2153b95926b3461d8721aef141f81362
Source dataset
uspto-grants-2008_04
Patent number
US07355040B2

Reaction notes

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