Trifluoroacetic acid → 5-carboxymethoxy-3-(1-naphthoyl)-N-pentyl-1H-indole

HRID 1399482Notes

Reaction equation

HRID 1399482 reaction equation
C([O:5][C:6]([CH2:8][O:9][C:10]1[CH:11]=[C:12]2[C:16](=[CH:17][CH:18]=1)[N:15]([CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])[CH:14]=[C:13]2[C:24]([C:26]1[C:35]2[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=2)[CH:29]=[CH:28][CH:27]=1)=[O:25])=[O:7])(C)(C)C.C(O)(C(F)(F)F)=O>ClCCl>[C:6]([CH2:8][O:9][C:10]1[CH:11]=[C:12]2[C:16](=[CH:17][CH:18]=1)[N:15]([CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])[CH:14]=[C:13]2[C:24]([C:26]1[C:35]2[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=2)[CH:29]=[CH:28][CH:27]=1)=[O:25])([OH:7])=[O:5]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 681592445-(tert-butoxycarbonylmethoxy)-3-(1-naphthoyl)-N-pentyl-1H-indole

Product 1

HCID 681593415-carboxymethoxy-3-(1-naphthoyl)-N-pentyl-1H-indole

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 7 (3.0 g, 6.4 mmol) in dichloromethane (50 ml) was added TFA (25 ml) and the mixture was stirred at room temperature for 3 h. The mixture was evaporated to dryness and the crude obtained was purified by chromatography on silica-gel using 5% methanol in chloroform to give Hapten-B (2.1 g, 79%).

Workup

  1. customThe mixture was evaporated to dryness
  2. customthe crude obtained
  3. customwas purified by chromatography on silica-gel
  4. customto give Hapten-B (2.1 g, 79%)

Sources & evidence

ORD record
ord-ce02093512aa43579f6398a31aac2b76
Source dataset
uspto-grants-2014_12
Patent number
US08906633B2

Reaction notes

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