Potassium Hydroxide → HCID 68860578, compound

HRID 898875Notes

Reaction equation

HRID 898875 reaction equation
[NH2:1][CH:2]1[CH2:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([S:11]C(=O)N(C)C)[CH:8]=2)[CH2:3]1.[OH-].[K+].Br[C:20]([CH3:29])([CH3:28])[C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22]>CO>[C:24]([O:23][C:21](=[O:22])[C:20]([S:11][C:7]1[CH:8]=[C:9]2[C:4](=[CH:5][CH:6]=1)[CH2:3][CH:2]([NH2:1])[CH2:10]2)([CH3:29])[CH3:28])([CH3:27])([CH3:26])[CH3:25]

Participants

5

Reactant 3

HCID 14797Potassium HydroxideHCID 90290tert-Butyl 2-bromo-2-methylpropionateHCID 59693403HCID 59693403, compound

Product 1

HCID 68860578HCID 68860578, compoundYield 76.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To dimethylthiocarbamic acid S-(2-aminoindan-5-yl) ester (4.9 g; 20.9 mmol), dissolved in MeOH (60 mL) is added a solution of KOH (11.8 g; 10 0.210 mol) in MeOH (110 mL) at RT. The solution is stirred at reflux for 5 h and cooled to RT. tert-Butyl 2-bromoisobutyrate (7.0 g; 31.3 mmol) is added to the solution and stirred for 18 h at RT. The solvent is evaporated under reduced pressure and the crude residue partitioned between H2O and EtOAc. The aqueous phase is extracted with EtOAc and the combined organic extracts were washed with H2O, brine, dried over Na2SO4, filtered and evaporated under reduced pressure to afford 4.9 g (76%) of 2-(2-aminoindan-5-ylsulfanyl)-2-methylpropionic acid tert-butyl ester as a brown oil.

Workup

  1. temperatureat reflux for 5 h
  2. stirringstirred for 18 h at RT
  3. customThe solvent is evaporated under reduced pressure
  4. customthe crude residue partitioned between H2O and EtOAc
  5. extractionThe aqueous phase is extracted with EtOAc
  6. washthe combined organic extracts were washed with H2O, brine
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-90231d70c0224b3eacd14cdf85ba2029
Source dataset
uspto-grants-2008_04
Patent number
US07351857B2

Reaction notes

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