Lithium Hydroxide → HCID 59505255, compound

HRID 1253657Notes

Reaction equation

HRID 1253657 reaction equation
[Li+].[OH-].[Cl:3][C:4]1[CH:30]=[CH:29][CH:28]=[CH:27][C:5]=1[C:6]([N:8]([C@H:14]1[C:22]2[C:17](=[CH:18][CH:19]=[C:20]([C:23]([O:25]C)=[O:24])[CH:21]=2)[CH2:16][CH2:15]1)[CH2:9][C:10]([F:13])([F:12])[F:11])=[O:7]>O.CO.C1COCC1>[Cl:3][C:4]1[CH:30]=[CH:29][CH:28]=[CH:27][C:5]=1[C:6]([N:8]([C@H:14]1[C:22]2[C:17](=[CH:18][CH:19]=[C:20]([C:23]([OH:25])=[O:24])[CH:21]=2)[CH2:16][CH2:15]1)[CH2:9][C:10]([F:12])([F:11])[F:13])=[O:7]

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 59505228HCID 59505228, compound

Product 1

HCID 59505255HCID 59505255, compoundYield 88%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 21899815MeOH tetrahydrofuranSolvent

Procedure

A solution of LiOH (153 mg, 3.64 mmol, 1.5 eq.) in water (8 ml) was added to a cooled (0° C.) solution of (R)-methyl 3-(2-chloro-N-(2,2,2-trifluoroethyl)benzamido)-2,3-dihydro-1H-indene-5-carboxylate (B-41) (1.0 g, 2.43 mmol, 1.0 eq.) in MeOH:THF (1:1, 16 ml) and the reaction mixture was then stirred at RT for 5 h. After completion of the reaction (monitored by TLC), the mixture was evaporated to dryness and diluted with water (15 ml). The aqueous layer was acidified to pH ˜3 using 1N HCl and then extracted with ethyl acetate (2×30 ml). The organic layer was washed with brine (20 ml), dried over anhydrous Na2SO4 and evaporated to afford the desired product as a white solid. Yield: 88% (850 mg, 2.14 mmol).

Workup

  1. customAfter completion of the reaction (monitored by TLC)
  2. customthe mixture was evaporated to dryness
  3. additiondiluted with water (15 ml)
  4. extractionextracted with ethyl acetate (2×30 ml)
  5. washThe organic layer was washed with brine (20 ml)
  6. dry with materialdried over anhydrous Na2SO4
  7. customevaporated

Sources & evidence

ORD record
ord-538c7d58bcb144d6bb02538f8a23463e
Source dataset
uspto-grants-2013_06
Patent number
US08455475B2

Reaction notes

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