Hydrochloric Acid → HCID 68460411, compound

HRID 501773Notes

Reaction equation

HRID 501773 reaction equation
[CH:1]1([O:6][C:7]2[CH:38]=[CH:37][C:10]([C:11]([C:13]3[CH:29]=[CH:28][C:16]([O:17][CH2:18][C:19]4[CH:27]=[CH:26][C:22]([C:23](O)=[O:24])=[CH:21][CH:20]=4)=[C:15]([CH2:30][CH2:31][C:32]([O:34][CH2:35][CH3:36])=[O:33])[CH:14]=3)=[O:12])=[C:9]([OH:39])[CH:8]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.C(N1C=CN=C1)(N1C=CN=C1)=O.[CH3:52][S:53]([NH2:56])(=[O:55])=[O:54].N12CCCN=C1CCCCC2.Cl>O1CCCC1.O.C(Cl)Cl>[CH:1]1([O:6][C:7]2[CH:38]=[CH:37][C:10]([C:11]([C:13]3[CH:29]=[CH:28][C:16]([O:17][CH2:18][C:19]4[CH:27]=[CH:26][C:22]([C:23]([NH:56][S:53]([CH3:52])(=[O:55])=[O:54])=[O:24])=[CH:21][CH:20]=4)=[C:15]([CH2:30][CH2:31][C:32]([O:34][CH2:35][CH3:36])=[O:33])[CH:14]=3)=[O:12])=[C:9]([OH:39])[CH:8]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

9

Reactant 5

HCID 313Hydrochloric AcidHCID 682631,1'-CarbonyldiimidazoleHCID 72879MethanesulfonamideHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 86598219HCID 86598219, compound

Product 1

HCID 68460411HCID 68460411, compoundYield 56.8%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

1.00 g of 4-{[4-[4-(cyclopentyloxy)-2-hydroxybenzoyl]-2-(3-ethoxy-3-oxopropyl)phenoxy]methyl} benzoic acid was dissolved in 12 mL of tetrahydrofuran, to which 1.03 g of 1,1′-carbonyldiimidazole was added at room temperature, and then this mixture was stirred for one hour while heating it under reflux. After the reaction mixture was cooled to room temperature, 1.07 g of methanesulfonamide and 1.7 mL of 1,8-diazabicyclo[5.4.0]undec-7-ene were added to this mixture, which was stirred for 30 minutes at room temperature and for another 30 minutes at 50° C. The reaction mixture which was cooled to room temperature was added to a mixture of methylene chloride and water, and adjusted to pH 2 with 6M hydrochloric acid, and then the organic phase was separated therefrom. After the resultant organic phase was washed with water and a saturated sodium chloride solution successively, this washed phase was dried over anhydrous magnesium sulfate and the solvent was distilled out under reduced pressure. The resultant residue was purified by silica gel column chromatography [eluent; hexane:ethyl acetate=1:2] to yield 0.65 g of ethyl 3-{5-[4-(cyclopentyloxy)-2-hydroxybenzoyl]-2-[(4-{[(methylsulfonyl)amino]carbonyl}benzyl)oxy]phenyl}propanoate as light yellow solid.

Workup

  1. additionwas added at room temperature
  2. temperaturewhile heating it
  3. temperatureunder reflux
  4. stirringwas stirred for 30 minutes at room temperature and for another 30 minutes at 50° C
  5. temperatureThe reaction mixture which was cooled to room temperature
  6. customthe organic phase was separated
  7. washAfter the resultant organic phase was washed with water
  8. dry with materiala saturated sodium chloride solution successively, this washed phase was dried over anhydrous magnesium sulfate
  9. distillationthe solvent was distilled out under reduced pressure
  10. customThe resultant residue was purified by silica gel column chromatography [eluent; hexane:ethyl acetate=1:2]

Sources & evidence

ORD record
ord-7f784add27844ed2ac1a8b78c08c88d9
Source dataset
uspto-grants-2010_08
Patent number
US07772285B2

Reaction notes

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