Water → Diphenylmethyl (4R, 6R, 7R)-3(1-hydroxybut 3enyl)7phenylacetamidoceph-2em-4carboxylate
Reaction equation
B(O)O.[C:4]([CH:7]([CH:9](C(O)=O)O)O)(O)=O.[CH:14]([C:16]1[C@H:21]([C:22]([O:24][CH:25]([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)=[O:23])[N:20]2[C:38](=[O:50])[C@@H:39]([NH:40][C:41](=[O:49])[CH2:42][C:43]3[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=3)[C@H:19]2[S:18][CH:17]=1)=[O:15].O.C(OCC)(=O)C>O1CCCC1>[OH:15][CH:14]([C:16]1[C@H:21]([C:22]([O:24][CH:25]([C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=2)[C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)=[O:23])[N:20]2[C:38](=[O:50])[C@@H:39]([NH:40][C:41](=[O:49])[CH2:42][C:43]3[CH:44]=[CH:45][CH:46]=[CH:47][CH:48]=3)[C@H:19]2[S:18][CH:17]=1)[CH2:9][CH:7]=[CH2:4]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 20 °C
Procedure
via a tartrate boronate. 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 warned 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
- temperaturecooled to −70° C.
- waitAfter 2 h at −70° C. the mixture was warned to 20° C.
- dry with materialThe organic layer was dried (MgSO4)
- customevaporated
- customthe residue purified by chromatography as in part
Sources & evidence
- ORD record
- ord-dfea567f78904328874f6b6797701dfc
- Source dataset
- uspto-grants-2008_04
- Patent number
- US07355040B2
Reaction notes
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