Sodium Hydroxide → HCID 131721978, compound

HRID 2306013Notes

Reaction equation

HRID 2306013 reaction equation
[C:1]([CH2:5][O:6][C:7]1[CH:12]=[C:11]([O:13][CH3:14])[CH:10]=[CH:9][C:8]=1[C@@H:15]1[C:23]2[C:18](=[CH:19][CH:20]=[C:21]([O:24][CH2:25][CH2:26][CH3:27])[CH:22]=2)[C@H:17]([C:28]2[CH:33]=[CH:32][C:31]3[O:34][CH2:35][O:36][C:30]=3[CH:29]=2)[C@H:16]1[C:37]([O:39]C)=[O:38])([O:3]C)=[O:2].[OH-].[Na+:42]>C(O)(C)C.O>[Na+:42].[Na+:42].[C:1]([CH2:5][O:6][C:7]1[CH:12]=[C:11]([O:13][CH3:14])[CH:10]=[CH:9][C:8]=1[C@@H:15]1[C:23]2[C:18](=[CH:19][CH:20]=[C:21]([O:24][CH2:25][CH2:26][CH3:27])[CH:22]=2)[C@H:17]([C:28]2[CH:33]=[CH:32][C:31]3[O:34][CH2:35][O:36][C:30]=3[CH:29]=2)[C@H:16]1[C:37]([O-:39])=[O:38])([OH:3])=[O:2].[C:1]([CH2:5][O:6][C:7]1[CH:12]=[C:11]([O:13][CH3:14])[CH:10]=[CH:9][C:8]=1[C@@H:15]1[C:23]2[C:18](=[CH:19][CH:20]=[C:21]([O:24][CH2:25][CH2:26][CH3:27])[CH:22]=2)[C@H:17]([C:28]2[CH:33]=[CH:32][C:31]3[O:34][CH2:35][O:36][C:30]=3[CH:29]=2)[C@H:16]1[C:37]([O-:39])=[O:38])([OH:3])=[O:2]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 9915481HCID 9915481, compound

Product 1

HCID 131721978HCID 131721978, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3776IsopropanolSolvent

Procedure

To a solution of (+) Methyl (1S,2R,3S)-3-(2-carbomethoxymethoxy-4-methoxyphenyl)-1-(3,4-methylenedioxyphenyl)-5-(prop-1-yloxy)indane-2-carboxylate (49.2 g) in isopropanol (1000 mL) and water (48 mL) was added a 50% aqueous solution of sodium hydroxide (179.4 g). The mixture was stirred under nitrogen for 16 hours then concentrated to approximately 200 mL. Water (400 mL) was added and the solution was extracted with t-butyl methyl ether (300 mL). The aqueous layer was acidified with dilute HCl and extracted twice with 300 mL portions of TBNE. The organic layer was washed 4 times with water (4×200 mL), then concentrated under reduced pressure. Absolute ethanol was added (400 mL) and the solution was further concentrated to approximately 150 mL. The solution was diluted to 800 mL with absolute ethanol and 60 mL of water. The solution was titrated to pH=11-12 with 1.25 N sodium hydroxide solution then after stirring for 15 minutes, concentrated to an oil. Absolute ethanol (250 mL) was added and the solution reconcentrated to a solid which was triturated with hexane, and filtered. The solid was dried to a constant weight to afford (+) (1S,2R,3S)-3-(2-carboxymethoxy-4-methoxyphenyl)-1-(3,4-methylenedioxyphenyl)-5-(prop-1-yloxy)indane-2-carboxylic acid disodium salt.

Workup

  1. concentrationthen concentrated to approximately 200 mL
  2. additionWater (400 mL) was added
  3. extractionthe solution was extracted with t-butyl methyl ether (300 mL)
  4. extractionextracted twice with 300 mL portions of TBNE
  5. washThe organic layer was washed 4 times with water (4×200 mL)
  6. concentrationconcentrated under reduced pressure
  7. additionAbsolute ethanol was added (400 mL)
  8. concentrationthe solution was further concentrated to approximately 150 mL
  9. additionThe solution was diluted to 800 mL with absolute ethanol and 60 mL of water
  10. stirringafter stirring for 15 minutes
  11. concentrationconcentrated to an oil
  12. additionAbsolute ethanol (250 mL) was added
  13. customwas triturated with hexane
  14. filtrationfiltered
  15. customThe solid was dried to a constant weight

Sources & evidence

ORD record
ord-1332d4a3043f4c03ade8d7077694c30d
Source dataset
uspto-grants-2002_08
Patent number
US06441173B1

Reaction notes

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