Lithium hydroxide, monohydrate → HCID 10199668, compound

HRID 992433Notes

Reaction equation

HRID 992433 reaction equation
ClC(Cl)(Cl)COC([N:7]1[C:19]2[CH2:18][N:17]([S:20]([CH2:23][C:24]3([C:30]([O:32]C)=[O:31])[CH2:29][CH2:28][O:27][CH2:26][CH2:25]3)(=[O:22])=[O:21])[CH2:16][CH2:15][C:14]=2[C:13]2[C:8]1=[CH:9][CH:10]=[CH:11][CH:12]=2)=O.O.[OH-].[Li+]>O1CCCC1.CO.O>[CH2:18]1[C:19]2[NH:7][C:8]3[C:13](=[CH:12][CH:11]=[CH:10][CH:9]=3)[C:14]=2[CH2:15][CH2:16][N:17]1[S:20]([CH2:23][C:24]1([C:30]([OH:32])=[O:31])[CH2:25][CH2:26][O:27][CH2:28][CH2:29]1)(=[O:21])=[O:22]

Participants

6

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 69895351HCID 69895351, compound

Product 1

HCID 10199668HCID 10199668, compoundYield 80.7%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

2-(4-Methoxycarbonyl-tetrahydro-pyran-4-ylmethanesulfonyl)-1,2,3,4-tetrahydro-β-carboline-9-carboxylic acid 2,2,2-trichloro-ethyl ester (556 mg) and lithium hydroxide monohydrate (206 mg) in tetrahydrofuran (10 ml), methanol (10 ml) and water (10 ml) was heated to reflux for 8 h. The reaction was left to stand at room temperature overnight and then refluxed for a further 4 h. The mixture was evaporated under reduced pressure and the residue dissolved in water (25 ml) and washed with ethyl acetate (2×30 ml). The aqueous was acidified to pH =4 with 5% citric acid solution and extracted with dichloromethane (2×40 ml) followed by ethyl acetate (3×50 ml). The combined extracts were dried (MgSO4) and evaporated under reduced pressure to give the title compound (299 mg, 80%) as a white solid.

Workup

  1. temperatureto reflux for 8 h
  2. waitThe reaction was left
  3. temperaturerefluxed for a further 4 h
  4. customThe mixture was evaporated under reduced pressure
  5. dissolutionthe residue dissolved in water (25 ml)
  6. washwashed with ethyl acetate (2×30 ml)
  7. extractionextracted with dichloromethane (2×40 ml)
  8. dry with materialThe combined extracts were dried (MgSO4)
  9. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-7209d649e31d426889ddfbc2782dab34
Source dataset
uspto-grants-2002_10
Patent number
US06469020B2

Reaction notes

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