Lithium Hydroxide → HCID 66863432, compound

HRID 2093428Notes

Reaction equation

HRID 2093428 reaction equation
[OH-].[Li+].C([O:5][C:6](=[O:38])[C:7]1[CH:12]=[C:11]([F:13])[CH:10]=[C:9]([NH:14][S:15]([CH2:18][CH:19]2[CH2:22][N:21]([CH:23]([C:31]3[CH:36]=[CH:35][C:34]([Cl:37])=[CH:33][CH:32]=3)[C:24]3[CH:29]=[CH:28][C:27]([Cl:30])=[CH:26][CH:25]=3)[CH2:20]2)(=[O:17])=[O:16])[CH:8]=1)C.O1CCCC1.P([O-])([O-])(O)=O.[Na+].[Na+]>C(OCC)C.O>[Cl:37][C:34]1[CH:35]=[CH:36][C:31]([CH:23]([C:24]2[CH:25]=[CH:26][C:27]([Cl:30])=[CH:28][CH:29]=2)[N:21]2[CH2:22][CH:19]([CH2:18][S:15]([NH:14][C:9]3[CH:8]=[C:7]([CH:12]=[C:11]([F:13])[CH:10]=3)[C:6]([OH:38])=[O:5])(=[O:16])=[O:17])[CH2:20]2)=[CH:32][CH:33]=1

Participants

7

Reactant 4

HCID 3939Lithium HydroxideHCID 8028TetrahydrofuranHCID 24203Sodium Phosphate, DibasicHCID 66864865HCID 66864865, compound

Product 1

HCID 66863432HCID 66863432, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Procedure

0.222 g of lithium hydroxide is added, in two parts, to a solution of 2.5 g of 3-({1-[bis(4-chlorophenyl)methyl]azetidin-3-yl}methanesulphonylamino)-5-fluorobenzoic acid ethyl ester in a mixture comprising 34 cm3 of tetrahydrofuran and 9 cm3 of water, stirred under an argon atmosphere. The reaction medium is stirred at a temperature in the region of 20° C. for 24 hours. 100 cm3 of a saturated aqueous solution of sodium hydrogen phosphate are then added so as to bring the pH to 5. The aqueous phase is extracted four times with 200 cm3 of ethyl acetate. The combined organic phases are dried over sodium sulphate, filtered through sintered glass and then concentrated to dryness under reduced pressure, to give a foam which is taken up twice with 150 cm3 of ethyl ether. After concentration under reduced pressure, 2.3 g of 3-({1-[bis(4-chlorophenyl)methyl]azetidin-3-yl}methanesulphonylamino)-5-fluorobenzoic acid are obtained in the form of a white solid.

Workup

  1. stirringThe reaction medium is stirred at a temperature in the region of 20° C. for 24 hours
  2. extractionThe aqueous phase is extracted four times with 200 cm3 of ethyl acetate
  3. dry with materialThe combined organic phases are dried over sodium sulphate
  4. filtrationfiltered through sintered glass
  5. concentrationconcentrated to dryness under reduced pressure
  6. customto give a foam which
  7. concentrationAfter concentration under reduced pressure, 2.3 g of 3-({1-[bis(4-chlorophenyl)methyl]azetidin-3-yl}methanesulphonylamino)-5-fluorobenzoic acid
  8. customare obtained in the form of a white solid

Sources & evidence

ORD record
ord-9cb144a0047e4d4791f919b6fa794f06
Source dataset
uspto-grants-2013_05
Patent number
US08445478B2

Reaction notes

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