Methanol → HCID 23691964, compound

HRID 546964Notes

Reaction equation

HRID 546964 reaction equation
CO.[OH-].[Na+:4].C[O:6][C:7](=[O:43])[CH2:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:20]=[CH:19][C:18]([C:21]([CH2:39][CH3:40])([C:24]3[CH:29]=[CH:28][C:27](/[CH:30]=[CH:31]/[C:32]4([OH:37])[CH2:36][CH2:35][CH2:34][CH2:33]4)=[C:26]([CH3:38])[CH:25]=3)[CH2:22][CH3:23])=[CH:17][C:16]=2[CH3:41])=[CH:11][C:10]=1[F:42].[Cl-].[NH4+]>O1CCCC1>[CH2:22]([C:21]([C:18]1[CH:19]=[CH:20][C:15]([C:12]2[CH:13]=[CH:14][C:9]([CH2:8][C:7]([O-:43])=[O:6])=[C:10]([F:42])[CH:11]=2)=[C:16]([CH3:41])[CH:17]=1)([C:24]1[CH:29]=[CH:28][C:27](/[CH:30]=[CH:31]/[C:32]2([OH:37])[CH2:36][CH2:35][CH2:34][CH2:33]2)=[C:26]([CH3:38])[CH:25]=1)[CH2:39][CH3:40])[CH3:23].[Na+:4]

Participants

6

Reactant 4

HCID 887MethanolHCID 14798Sodium HydroxideHCID 25517Ammonium ChlorideHCID 57709041HCID 57709041, compound

Product 1

HCID 23691964HCID 23691964, compoundYield 57%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Methanol (1.3 mL), tetrahydrofuran (1.3 mL) and a 1 M sodium hydroxide aqueous solution (0.129 mL, 0.129 mmol) were added to [4′-(1-ethyl-1-{4-[(E)-2-(1-hydroxy-cyclopentyl)-vinyl]-3-methyl-phenyl}-propyl)-3-fluoro-2′-methyl-biphenyl-4-yl]-acetic acid methyl ester (Example 84-(1); 22.8 mg, 0.043 mmol), and the mixture was stirred at room temperature for 25 hours. The reaction solution was poured into a saturated aqueous ammonium chloride solution, and then the aqueous layer was extracted with dichloromethane. The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was crudely purified by preparative TLC (chloroform/methanol=10/1). The crude purified product was diluted with methanol. After addition of sodium methoxide, the mixture was dried under reduced pressure. The residue was purified by preparative TLC (developer obtained by saturating chloroform/methanol=10/1 with water). The purified product was diluted with methanol. After addition of sodium methoxide, the mixture was dried under reduced pressure to give the title compound (12.6 mg, 57%).

Workup

  1. extractionthe aqueous layer was extracted with dichloromethane
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was crudely purified by preparative TLC (chloroform/methanol=10/1)
  5. customThe crude purified product
  6. additionwas diluted with methanol
  7. additionAfter addition of sodium methoxide
  8. customthe mixture was dried under reduced pressure
  9. customThe residue was purified by preparative TLC (developer obtained by saturating chloroform/methanol=10/1 with water)
  10. additionThe purified product was diluted with methanol
  11. additionAfter addition of sodium methoxide
  12. customthe mixture was dried under reduced pressure

Sources & evidence

ORD record
ord-cae3a927d6784ae681c34e03b2f2401b
Source dataset
uspto-grants-2011_05
Patent number
US07935688B2

Reaction notes

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