Trifluoroacetic acid → HCID 9885288, compound

HRID 843127Notes

Reaction equation

HRID 843127 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[O:7][C:8]2[CH:17]=[CH:16][CH:15]=[C:14]([O:18][CH2:19][CH2:20][CH2:21][N:22](C(OC(C)(C)C)=O)[C:23]([CH3:26])([CH3:25])[CH3:24])[C:9]=2[C:10]=1[CH2:11][CH2:12][CH3:13])=[O:5])[CH3:2].FC(F)(F)C(O)=O>ClCCl>[CH2:1]([O:3][C:4]([C:6]1[O:7][C:8]2[CH:17]=[CH:16][CH:15]=[C:14]([O:18][CH2:19][CH2:20][CH2:21][NH:22][C:23]([CH3:25])([CH3:24])[CH3:26])[C:9]=2[C:10]=1[CH2:11][CH2:12][CH3:13])=[O:5])[CH3:2]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 54153301HCID 54153301, compound

Product 1

HCID 9885288HCID 9885288, compoundYield 61.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a dichloromethane (0.5 ml) solution of 4-[3-(tert-butoxycarbonyl-tert-butyl-amino)-propoxy]-3-propyl-benzofuran-2-carboxylic acid ethyl ester (5.0 mg) was added trifluoroacetic acid (0.5 ml) at room temperature. After stirring overnight, the reaction mixture was concentrated in vacuo to dryness. The residue was purified by silica gel column chromatography developed by dichloromethane-methanol to give 4-(3-tert-butylamino-propoxy)-3-propyl-benzofuran-2-carboxylic acid ethyl ester (2.4 mg) as a pale yellow oil. FAB-MS: m/z 362 (MH+); 1H-NMR (CDCl3): δ 0.91 (3H, t, J=7.3 Hz), 1.34 (s, 9H), 1.25-1.45 (5H, m), 1.64 (2H, quintet, J=7.3 Hz), 2.23 (2H, quintet, J=7.3 Hz), 3.07 (2H, t, J=7.3 Hz), 3.16 (2H, t, J=7.3 Hz), 4.09 (2H, t, J=5.9 Hz), 4.42 (2H, q, J=6.9 Hz), 6.52 (1H, d, J=8.3 Hz), 7.12 (1H, d, J=8.3 Hz), 7.28 (1H, dd, J=8.3 Hz, 8.3 Hz).

Workup

  1. concentrationthe reaction mixture was concentrated in vacuo to dryness
  2. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-7ee86718084747179a3b6fa004b9429c
Source dataset
uspto-grants-2002_04
Patent number
US06376491B1

Reaction notes

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