Trifluoroacetic acid → HCID 89816040, compound

HRID 1468901Notes

Reaction equation

HRID 1468901 reaction equation
C(OC(=O)[NH:7][CH2:8][CH2:9][N:10]1[C:18]2[C:13](=[CH:14][CH:15]=[C:16]([S:19][CH3:20])[CH:17]=2)[CH:12]=[C:11]1[C:21](=[O:25])[CH:22]([CH3:24])[CH3:23])(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH2:7][CH2:8][CH2:9][N:10]1[C:18]2[C:13](=[CH:14][CH:15]=[C:16]([S:19][CH3:20])[CH:17]=2)[CH:12]=[C:11]1[C:21](=[O:25])[CH:22]([CH3:23])[CH3:24]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 89827882HCID 89827882, compound

Product 1

HCID 89816040HCID 89816040, compoundYield 143.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl(2-(2-isobutyryl-6-(methylthio)-1H-indol-1-yl)ethyl)carbamate (200 mg, 0.53 mmol) in CH2Cl2 (9 mL) at 0° C. was added TFA (1 mL). The reaction mixture was stirred at rt for 1 h. The mixture was concentrated (T<25° C.), treated with water (5 mL), adjusted to pH=11 with sat. NaHCO3 and extracted with EtOAc (20 mL×3). The combined organic layers were dried over anhydrous Na2SO4, filtered, concentrated to afford 1-(1-(2-aminoethyl)-6-(methylthio)-1H-indol-2-yl)-2-methylpropan-1-one (210 mg, 100% yield) as a colorless oil. LC-MS MS (ESI) m/z 258.8 [M−18+H]+.

Workup

  1. concentrationThe mixture was concentrated (T<25° C.)
  2. additiontreated with water (5 mL)
  3. extractionextracted with EtOAc (20 mL×3)
  4. dry with materialThe combined organic layers were dried over anhydrous Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-35ade1c966004a50b74b0d75d6e2bc56
Source dataset
uspto-grants-2015_04
Patent number
US09006244B2

Reaction notes

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