Trifluoroacetic acid → HCID 89816040, compound

HRID 1051823Notes

Reaction equation

HRID 1051823 reaction equation
[C:1]([C:6]1[N:7]([CH2:17][CH2:18][NH:19]C(=O)OC(C)(C)C)[C:8]2[C:13]([CH:14]=1)=[CH:12][CH:11]=[C:10]([S:15][CH3:16])[CH:9]=2)(=[O:5])[CH:2]([CH3:4])[CH3:3].C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH2:19][CH2:18][CH2:17][N:7]1[C:8]2[C:13](=[CH:12][CH:11]=[C:10]([S:15][CH3:16])[CH:9]=2)[CH:14]=[C:6]1[C:1](=[O:5])[CH:2]([CH3:3])[CH3:4]

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-a74a4d57dcdd49bcae6a46985b99c581
Source dataset
uspto-grants-2016_07
Patent number
US09388190B2

Reaction notes

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