Pyrrolidine → HCID 22093459, compound

HRID 2229547Notes

Reaction equation

HRID 2229547 reaction equation
C([O:4][C:5](=[O:30])[CH2:6][O:7][C:8]1[CH:13]=[CH:12][C:11]([NH:14][C:15](=[O:17])[CH3:16])=[CH:10][C:9]=1[C:18](=[O:29])[NH:19][CH2:20][C:21]1[CH:26]=[CH:25][C:24]([Br:27])=[CH:23][C:22]=1[F:28])C=C.N1CCCC1>O.O1CCOCC1.C(OCC)(=O)C>[C:15]([NH:14][C:11]1[CH:12]=[CH:13][C:8]([O:7][CH2:6][C:5]([OH:30])=[O:4])=[C:9]([C:18](=[O:29])[NH:19][CH2:20][C:21]2[CH:26]=[CH:25][C:24]([Br:27])=[CH:23][C:22]=2[F:28])[CH:10]=1)(=[O:17])[CH3:16]

Participants

6

Reactant 2

HCID 31268PyrrolidineHCID 22093472HCID 22093472, compound

Product 1

HCID 22093459HCID 22093459, compoundYield 52.2%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of [4-acetylamino-2-(4-bromo-2-fluoro-benzylcarbamoyl)-phenoxy]-acetic acid allyl ester (0.114 g, 0.24 mmol) in 10% H2O in 1,4-dioxane (8 mL, 0.03 M) was treated with pyrollidine (0.05 mL, 0.60 mmol) and [(C6H5)3P]4Pd (0.01 g, 3.6 mol%) was stirred for 6 h. The reaction was diluted with ethyl acetate and washed with 2 N HCl (3×), H2O (2×), saturated aq NaCl, dried over MgSO4, filtered, concentrated and recrystallized from heptane and ethyl acetate to give [4-acetylamino-2-(4-bromo-2-fluoro-benzylcarbamoyl)-phenoxy]-acetic acid (0.055 g, 52%) as a white solid: mp 235° C.; 1H NMR (DMSO-d6, 300 MHz) δ 9.93 (br s, 1H), 9.16 (br t, 1H), 7.98 (br d, J=2.7 Hz, 1H), 7.73 (br dd, J1=9.0 Hz, J2=2.7 Hz, 1 H), 7.44-7.20 (m, 2H), 7.20-7.00 (m, 2H), 4.80 (s, 2H), 4.54 br d, J=4.5 Hz, 2H), 1.99 (s, 3H).

Workup

  1. washwashed with 2 N HCl (3×), H2O (2×), saturated aq NaCl
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customrecrystallized from heptane and ethyl acetate

Sources & evidence

ORD record
ord-fe4a13e97bd84971a49f477adfa2709e
Source dataset
uspto-grants-2002_07
Patent number
US06420426B1

Reaction notes

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