HCID 86600789, compound → HCID 69047710, compound
Reaction equation
C([O:3][C:4]([C@@H:6]1[C@@H:10]([C:11](=[O:20])[NH:12][C:13]2[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][CH:14]=2)[CH2:9][N:8]([S:21]([CH3:24])(=[O:23])=[O:22])[CH2:7]1)=[O:5])C>O1CCOCC1.O>[Cl:19][C:16]1[CH:17]=[CH:18][C:13]([NH:12][C:11]([C@H:10]2[CH2:9][N:8]([S:21]([CH3:24])(=[O:23])=[O:22])[CH2:7][C@@H:6]2[C:4]([OH:5])=[O:3])=[O:20])=[CH:14][CH:15]=1Participants
3
Reactant 1
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 25 °C
Procedure
Compound 39d (0.9 g; 2.4 mmol) is dissolved in a mixture of 1,4-dioxane/water (1:1; 15 ml). LiOH monohydrate (0.302 g; 7.2 mmol) is added as a solid and the mixture is stirred for 18 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: 0.7 g (84.1%), ESI-MS: m/z=345 [M−H]−, Cl-pattern
Workup
- 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-2c27658e608a46fa812335d4b2a6c501
- Source dataset
- uspto-grants-2009_06
- Patent number
- US07550487B2
Reaction notes
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