HCID 86600788, compound → HCID 69048291, compound
Reaction equation
C([O:3][C:4]([C@@H:6]1[C@@H:10]([C:11](=[O:27])[NH:12][C:13]2[CH:18]=[CH:17][C:16]([N:19]3[CH:24]=[CH:23][CH:22]=[CH:21][C:20]3=[O:25])=[CH:15][C:14]=2[F:26])[CH2:9][N:8]([S:28]([CH3:31])(=[O:30])=[O:29])[CH2:7]1)=[O:5])C>O1CCOCC1.O>[F:26][C:14]1[CH:15]=[C:16]([N:19]2[CH:24]=[CH:23][CH:22]=[CH:21][C:20]2=[O:25])[CH:17]=[CH:18][C:13]=1[NH:12][C:11]([C@H:10]1[CH2:9][N:8]([S:28]([CH3:31])(=[O:30])=[O:29])[CH2:7][C@@H:6]1[C:4]([OH:5])=[O:3])=[O:27]Participants
3
Reactant 1
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 25 °C
Procedure
Compound 28d (3.7 g; 8 mmol) is dissolved in a mixture of 1,4-dioxane/water (1:1; 30 ml). LiOH monohydrate (1.03 g; 25 mmol) is added to the mixture and complete saponification is obtained after stirring for 24 h at 25° C. The mixture is evaporated to dryness and dissolved in ethyl acetate and the product is extracted with saturated aqueous Na2CO3 solution. The aqueous phase is cooled to 10° C. and acidified with 25% aqueous HCl solution until pH=1. The product is extracted several times with ethylacetate (3×100 ml). The combined organic phases are washed with brine and dried over Na2SO4. After filtration the organic phase is evaporated to dryness. Yield: 1.57 g (45.2%), ESI-MS: m/z=422 [M−H]−
Workup
- customcomplete saponification is obtained
- customThe mixture is evaporated to dryness
- dissolutiondissolved in ethyl acetate
- extractionthe product is extracted with saturated aqueous Na2CO3 solution
- temperatureThe aqueous phase is cooled to 10° C.
- extractionThe product is extracted several times with ethylacetate (3×100 ml)
- washThe combined organic phases are washed with brine
- dry with materialdried over Na2SO4
- filtrationAfter filtration the organic phase
- customis evaporated to dryness
Sources & evidence
- ORD record
- ord-4ca13aaa0f72432fa613034416199455
- Source dataset
- uspto-grants-2009_06
- Patent number
- US07550487B2
Reaction notes
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