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

HRID 55928Notes

Reaction equation

HRID 55928 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH2:11][CH2:12][CH2:13][CH2:14][CH3:15])[CH:6]=[C:5]2[C:16]([C:18]1[C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[CH:21]=[CH:20][CH:19]=1)=[O:17].[C:28]([OH:34])([C:30](F)(F)F)=[O:29]>ClCCl>[C:28]([CH2:30][O:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH2:11][CH2:12][CH2:13][CH2:14][CH3:15])[CH:6]=[C:5]2[C:16]([C:18]1[C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[CH:21]=[CH:20][CH:19]=1)=[O:17])([OH:34])=[O:29]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 53394447JWH 018 5-hydroxyindole metabolite

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-7d99fefe344d435782ca7a1b917eab47
Source dataset
uspto-grants-2016_09
Patent number
US09434687B2

Reaction notes

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