Trifluoroacetic acid → Ethyl 6-[4-(4-pyridylamino)phenoxy]hexanoate

HRID 1290532Notes

Reaction equation

HRID 1290532 reaction equation
FC(F)(F)C(O)=O.[N:8]1[CH:13]=[CH:12][C:11]([N:14]([C:22]2[CH:38]=[CH:37][C:25]([O:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][C:32]([O:34][CH2:35][CH3:36])=[O:33])=[CH:24][CH:23]=2)C(OC(C)(C)C)=O)=[CH:10][CH:9]=1>ClCCl>[N:8]1[CH:13]=[CH:12][C:11]([NH:14][C:22]2[CH:23]=[CH:24][C:25]([O:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][C:32]([O:34][CH2:35][CH3:36])=[O:33])=[CH:37][CH:38]=2)=[CH:10][CH:9]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 18918347ethyl 6-[4-[N-(4-pyridyl)-N-tertiary-butyloxycarbonylamino]phenoxy]hexanoate

Product 1

HCID 18918592Ethyl 6-[4-(4-pyridylamino)phenoxy]hexanoate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (3 ml) was added to a stirred solution of ethyl 6-[4-[N-(4-pyridyl)-N-tertiary-butyloxycarbonylamino]phenoxy]- hexanoate (260 mg) dissolved in dichloromethane (3 ml). After 18 hours the solvents were removed in vacuo and the residual gum dissolved in dichloromethane. This solution was treated with a saturated solution of sodium hydrogen carbonate. The organic phase was washed with water, dried and evaporated. Trituration of the residue with hexane gave the title compound, 120 mg, as a white solid: m.p. 104°-106° C.; NMR (CDCl3) δ8.22(2H,d), 7.12(2H,d), 6.90(2H,d), 6.64(2H,dd), 5.82(1H,s), 4.13(2H,q), 3.97(2H,t), 2.34(2H,t), 1.80(2H,m), 1.70(2H,m), 1.53(2H,m), 1.27(3H,t); m/e 329 (M+H)+ ; calculated for C19H24N2O3.0.25H2O:C, 68.6; H, 7.4; N, 8.4. found: C, 68.8; H, 7.3; N, 8.2%.

Workup

  1. customAfter 18 hours the solvents were removed in vacuo
  2. dissolutionthe residual gum dissolved in dichloromethane
  3. additionThis solution was treated with a saturated solution of sodium hydrogen carbonate
  4. washThe organic phase was washed with water
  5. customdried
  6. customevaporated

Sources & evidence

ORD record
ord-9332cb2a21304f8c9b4b63d385f40f97
Source dataset
uspto-grants-1998_05
Patent number
US05750754

Reaction notes

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