Trifluoroacetic acid → HCID 46899294, compound

HRID 602792Notes

Reaction equation

HRID 602792 reaction equation
C(OC([N:8]1[C:20]2[CH2:19][CH:18]([C:21]([S:27]([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)(=[O:29])=[O:28])([C:23]([O:25][CH3:26])=[O:24])[CH3:22])[CH2:17][CH2:16][C:15]=2[C:14]2[C:9]1=[CH:10][CH:11]=[C:12]([N:36]([CH3:38])[CH3:37])[CH:13]=2)=O)(C)(C)C.C(O)(C(F)(F)F)=O.C([O-])(O)=O.[Na+]>C(Cl)Cl>[CH3:26][O:25][C:23](=[O:24])[C:21]([S:27]([C:30]1[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=1)(=[O:29])=[O:28])([CH:18]1[CH2:17][CH2:16][C:15]2[C:14]3[C:9](=[CH:10][CH:11]=[C:12]([N:36]([CH3:37])[CH3:38])[CH:13]=3)[NH:8][C:20]=2[CH2:19]1)[CH3:22]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 67266801HCID 67266801, compound

Product 1

HCID 46899294HCID 46899294, compoundYield 56%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 42 mg (9.3 mmol) of (RS,SR)-2-(-1-benzenesulfonyl-1-methoxycarbonyl-ethyl)-6-dimethylamino-1,2,3,4-tetrahydro-carbazole-9-carboxylic acid tert-butyl ester in 1 ml of CH2Cl2 were added 0.06 ml of TFA at 0° C. The solution was stirred at RT for 5 h, a NaHCO3 solution was added, and the inorganic phase was extracted with CH2Cl2, washed with brine and dried over Na2SO4. Column chromatography on ISOLUTE Flash NH2 (Separtis, aminopropyl-modified silicagel) with EtOAc/heptane 2:1, followed by tituration with ether/heptane yielded 190 mg (56%) of (RS,SR)-2-benzenesulfonyl-2-(6-dimethylamino-2,3,4,9-tetrahydro-1H-carbazol-2-yl)-propionic acid methyl ester as light green amorphous material, MS: 441 (MH+).

Workup

  1. extractionthe inorganic phase was extracted with CH2Cl2
  2. washwashed with brine
  3. dry with materialdried over Na2SO4

Sources & evidence

ORD record
ord-39c2c21963c84996814823579293c3cc
Source dataset
uspto-grants-2011_03
Patent number
US07906546B2

Reaction notes

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