Water → Diphenylmethyl (4R, 6R, 7R)-3(1-hydroxybut 3enyl)7phenylacetamidoceph-2em-4carboxylate

HRID 2417153Notes

Reaction equation

HRID 2417153 reaction equation
[CH:1]([C:3]1[C@H:8]([C:9]([O:11][CH:12]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[O:10])[N:7]2[C:25](=[O:37])[C@@H:26]([NH:27][C:28](=[O:36])[CH2:29][C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)[C@H:6]2[S:5][CH:4]=1)=[O:2].O.C(OCC)(=O)C.O1C[CH2:48][CH2:47][CH2:46]1>>[OH:2][CH:1]([C:3]1[C@H:8]([C:9]([O:11][CH:12]([C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)[C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[O:10])[N:7]2[C:25](=[O:37])[C@@H:26]([NH:27][C:28](=[O:36])[CH2:29][C:30]3[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=3)[C@H:6]2[S:5][CH:4]=1)[CH2:48][CH:47]=[CH2:46]

Participants

5

Reactant 4

HCID 962WaterHCID 8028TetrahydrofuranHCID 8857Ethyl AcetateHCID 113527753-Formyl-7betaphenylacetylamino-ceph-2-em-4alpha-carboxylic acid diphenylmethyl ester

Product 1

HCID 131724666Diphenylmethyl (4R, 6R, 7R)-3(1-hydroxybut 3enyl)7phenylacetamidoceph-2em-4carboxylate

Conditions

Temperature
20 °C

Procedure

A mixture of dimethyl (R,R)-2-allyl-1,3,2-dixoaborolane-4,5-dicarboxylate (0.67M in toluene, 1.8 ml, 1.2 mmol) and 0.4 nm molecular sieves (50 mg) was stirred at 20° C. for 10 minutes and then cooled to −70° C., and then a solution of diphenylmethyl (4R, 6R, 7R)-3-formyl-7-phenylacetamidoceph-2-em-4-carboxylate (100 mg, 0.2 mmol) in tetrahydrofuran (0.5 ml) was added dropwise. After 2 h at −70° C. the mixture was warmed to 20° C. and water and ethyl acetate were added. The organic layer was dried (MgSO4) and evaporated and the residue purified by chromatography as in part a to give the title compound S-diastereomer, 45 mg (43%), and the R-diastereomer 8 mg (8%).

Workup

  1. temperaturecooled to −70° C.
  2. temperatureAfter 2 h at −70° C. the mixture was warmed to 20° C.
  3. dry with materialThe organic layer was dried (MgSO4)
  4. customevaporated
  5. customthe residue purified by chromatography as in part

Sources & evidence

ORD record
ord-11fe0820341f428ebf27dc77973313dd
Source dataset
uspto-grants-2004_11
Patent number
US06825344B2

Reaction notes

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