Lithium Hydroxide → HCID 58160343, compound

HRID 1516986Notes

Reaction equation

HRID 1516986 reaction equation
[Li+].[OH-].[Cl:3][C:4]1[CH:9]=[CH:8][C:7]([S:10][C:11]2[C:19]3[C:18](=[O:20])[CH2:17][CH2:16][CH2:15][C:14]=3[N:13]([CH2:21][C:22]([O:24]CC)=[O:23])[C:12]=2[CH3:27])=[CH:6][CH:5]=1>C1COCC1.CO>[Cl:3][C:4]1[CH:9]=[CH:8][C:7]([S:10][C:11]2[C:19]3[C:18](=[O:20])[CH2:17][CH2:16][CH2:15][C:14]=3[N:13]([CH2:21][C:22]([OH:24])=[O:23])[C:12]=2[CH3:27])=[CH:6][CH:5]=1

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 58160346HCID 58160346, compound

Product 1

HCID 58160343HCID 58160343, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of LiOH (1.79 g, 1.77 g corrected for assay, 42.2 mmol) was added to a stirred solution of ethyl [3-(4-chlorophenylsulfanyl)-2-methyl-4-oxo-4,5,6,7-tetrahydro-1H-indol-1-yl]acetate (7.5 g, 5.33 g corrected for assay, 14.1 mmol) in a mixture of THF (27 mL) and MeOH (27 mL). The mixture was stirred for 1 h. The solvents were removed in vacuo (45 mbar) at 45° C. until the volume of the mixture was ˜20 mL. Water (27 mL) and CH2Cl2 (27 mL) was added and the mixture stirred for 5 mins. The layers were allowed to separate, concentrated aqueous hydrochloric acid (5 mL) was added to the aqueous layer and the resulting solid product was collected by filtration and washed with water (5 mL). This crude damp product was slurried in a mixture of EtOAc (20 mL), CH5Cl2 (20 mL) and heptane (20 mL) at r.t. The product was dried briefly on the filter to give the title compound; 4.64 g; assay by 1H NMR: 89.3% w/w; yield corrected for assay: 4.14 g (84%); purity by LC 99.1 area %; m/z: 350 (MH+); 1H NMR: 1.99-2.05 (2H, m), 2.16 (3H, s), 2.26-2.31 (2H, t), 2.73-2.77 (2H, t), 4.83 (2H, s), 6.95-6.99 (2H, d), 7.23-7.27 (2H, d).

Workup

  1. customThe solvents were removed in vacuo (45 mbar) at 45° C. until the volume of the mixture
  2. additionWater (27 mL) and CH2Cl2 (27 mL) was added
  3. stirringthe mixture stirred for 5 mins
  4. customto separate
  5. additionconcentrated aqueous hydrochloric acid (5 mL) was added to the aqueous layer
  6. filtrationthe resulting solid product was collected by filtration
  7. washwashed with water (5 mL)
  8. additionThis crude damp product was slurried in a mixture of EtOAc (20 mL), CH5Cl2 (20 mL) and heptane (20 mL) at r.t
  9. customThe product was dried briefly on the
  10. filtrationfilter

Sources & evidence

ORD record
ord-fc9a6cd3e4f045bea343915eb23f32bb
Source dataset
uspto-grants-2012_07
Patent number
US08227622B2

Reaction notes

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