Trifluoroacetic acid → 2-(6-Methoxy-1,3,4,9-tetrahydro-beta-carboline-2-sulfonylmethyl)-3-methylbutyric acid

HRID 992431Notes

Reaction equation

HRID 992431 reaction equation
FC(F)(F)C(O)=O.C([O:12][C:13](=[O:37])[CH:14]([CH2:18][S:19]([N:22]1[CH2:34][CH2:33][C:32]2[C:31]3[C:26](=[CH:27][CH:28]=[C:29]([O:35][CH3:36])[CH:30]=3)[NH:25][C:24]=2[CH2:23]1)(=[O:21])=[O:20])[CH:15]([CH3:17])[CH3:16])(C)(C)C.ClCCl.CO>ClCCl>[CH3:36][O:35][C:29]1[CH:30]=[C:31]2[C:26](=[CH:27][CH:28]=1)[NH:25][C:24]1[CH2:23][N:22]([S:19]([CH2:18][CH:14]([CH:15]([CH3:17])[CH3:16])[C:13]([OH:37])=[O:12])(=[O:21])=[O:20])[CH2:34][CH2:33][C:32]2=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 21226129Dichloromethane methanolHCID 698956642-(6-Methoxy-1,3,4,9-tetrahydro-beta-carboline-2-sulfonylmethyl)-3-methylbutyric acid tert-butyl ester

Product 1

HCID 101778142-(6-Methoxy-1,3,4,9-tetrahydro-beta-carboline-2-sulfonylmethyl)-3-methylbutyric acidYield 62%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (1 ml) was added to a solution of 2-(6-methoxy-1,3,4,9-tetrahydro-β-carboline-2-sulfonylmethyl)-3-methyl-butyric acid tert-butyl ester (237 mg) in dichloromethane (10 ml) at room temperature under nitrogen. The mixture was stirred for 2 h before being evaporated under reduced pressure. The residue was partitioned between 1M aqueous sodium hydroxide (15 ml) and diethyl ether (15 ml). The organics were extracted with 1M aqueous sodium hydroxide (15 ml). The combined aqueous portions were acidified to pH=5 with 10% citric acid and extracted with ethyl acetate (4×20 ml). The combined organics were washed with water (2×10 ml) and brine (10 ml), then dried (MgSO4), filtered and the solvent removed under reduced pressure to give, after chromatography (SiO2, 20:1 dichloromethane-methanol), the title compound (128 mg, 62%) as a white foam.

Workup

  1. custombefore being evaporated under reduced pressure
  2. customThe residue was partitioned between 1M aqueous sodium hydroxide (15 ml) and diethyl ether (15 ml)
  3. extractionThe organics were extracted with 1M aqueous sodium hydroxide (15 ml)
  4. extractionextracted with ethyl acetate (4×20 ml)
  5. washThe combined organics were washed with water (2×10 ml) and brine (10 ml)
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. customthe solvent removed under reduced pressure
  9. customto give

Sources & evidence

ORD record
ord-b92edcc3c2564bde80ef27719463e224
Source dataset
uspto-grants-2002_10
Patent number
US06469020B2

Reaction notes

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