Hydrochloric Acid → HCID 58975595, compound

HRID 2111139Notes

Reaction equation

HRID 2111139 reaction equation
[F:1][C:2]([F:31])([F:30])[CH2:3][O:4][CH2:5][C:6]1[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[O:8][C:7]=1[C:15]([NH:17][CH2:18][CH2:19][O:20][C:21]1[CH:29]=[CH:28][C:24]([C:25]([O-])=[O:26])=[CH:23][CH:22]=1)=[O:16].[NH2:32][OH:33].[OH-].[Na+].Cl>CO>[OH:33][NH:32][C:25](=[O:26])[C:24]1[CH:28]=[CH:29][C:21]([O:20][CH2:19][CH2:18][NH:17][C:15]([C:7]2[O:8][C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=3[C:6]=2[CH2:5][O:4][CH2:3][C:2]([F:31])([F:30])[F:1])=[O:16])=[CH:22][CH:23]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 787HydroxylamineHCID 14798Sodium HydroxideHCID 86600352HCID 86600352, compound

Product 1

HCID 58975595HCID 58975595, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

4-{2-[3-(2,2,2-Trifluoroethoxymethyl)benzofuran-2-yl-carbonylamino]-ethoxy}-benzoate was dissolved in MeOH and excess aqueous hydroxylamine solution and NaOH(aq) were added to give pH 10-11. After stirring overnight, the reaction mixture was neutralized reaction to pH 7-8 with aqueous hydrochloric acid. The reaction mixture was concentrated in vacuo to give a solid which was collected and washed with water, then dissolved in acetonitrile and water and purified with prep HPLC to give the title compound (35 mg). 1H NMR (400 MHz, DMSO-d6) δ 11.04 (s, 1H), 8.95 (t, J=5.6 Hz, 1H), 8.89 (s, 1H), 7.81 (d, J=7.6 Hz, 1H), 7.70 (d, J=8.8 Hz, 2H), 7.63 (d, J=8.8 Hz, 1H), 7.50 (t, J=8.8 Hz, 1H), 7.36 (t, J=8.0 Hz, 1H), 7.00 (d, J=9.2 Hz, 2H), 5.25 (s, 2H), 4.18 (m, 4H), 3.67 (m, 2H). EM (calc.): 452.1; MS (ESI) m/e (M+1H)+: 453.0, (M−1H)−: 451.0.

Workup

  1. customto give pH 10-11
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. customto give a solid which
  4. customwas collected
  5. washwashed with water
  6. dissolutiondissolved in acetonitrile
  7. customwater and purified with prep HPLC

Sources & evidence

ORD record
ord-f175a333fd784dcbaec6480d5b915368
Source dataset
uspto-grants-2009_04
Patent number
US07517988B2

Reaction notes

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