Sodium Hydroxide → HCID 22093453, compound

HRID 2229577Notes

Reaction equation

HRID 2229577 reaction equation
C([O:3][C:4](=[O:32])[CH2:5][O:6][C:7]1[CH:12]=[C:11]([F:13])[C:10]([N:14]2[CH2:19][CH2:18][O:17][CH2:16][CH2:15]2)=[CH:9][C:8]=1[C:20](=[O:31])[NH:21][CH2:22][C:23]1[CH:28]=[CH:27][C:26]([Br:29])=[CH:25][C:24]=1[F:30])C.[OH-].[Na+]>C(O)C>[Br:29][C:26]1[CH:27]=[CH:28][C:23]([CH2:22][NH:21][C:20]([C:8]2[CH:9]=[C:10]([N:14]3[CH2:19][CH2:18][O:17][CH2:16][CH2:15]3)[C:11]([F:13])=[CH:12][C:7]=2[O:6][CH2:5][C:4]([OH:32])=[O:3])=[O:31])=[C:24]([F:30])[CH:25]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 22093480HCID 22093480, compound

Product 1

HCID 22093453HCID 22093453, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A suspension of [2-(4-bromo-2-fluoro-benzylcarbamoyl)-5-fluoro-4-morpholin-4-yl-phenoxy]-acetic acid ethyl ester (0.8 g, 1.73 mmol) in ethanol (9 mL) was treated with aq 2 N NaOH (5.0 mL, 10.4 mmol). After stirring for 30 min, the reaction was concentrated in vacuo until most of the ethanol was removed. The mixture was acidified to pH 3 with aq 2 N HCl, extrated with ethyl acetate, and washed with saturated NaCl. The organic layer was dried over MgSO4, filtered and concentrated to give [2-(4-bromo-2-fluoro-benzylcarbamoyl)-5-fluoro-4-morpholin-4-yl-phenoxy]-acetic acid (0.7 g, 93%) as a white crystalline solid: mp 180° C.; Rf 0.17 (20% methanol in dichloromethane); 1H NMR (DMSO-d6 300 MHz) δ 9.21 (t, J=5.4 Hz, 1H), 8.17 (s, 1H), 8.09 (dd, J1=8.1 Hz, J2=2.4 Hz, 1H), 7.78 (d, J=7.5 Hz, 1H), 7.65-7.52 (m, 2H), 7.13 (d, J=13.8 Hz, 1H), 4.85 (s, 2H), 4.62 (d, J=6 Hz, 2H), 3.71 (t, J=4.7 Hz, 4H), 2.91 (t, J=4.8 Hz, 4H). Anal. calcd for C20H20FN3O7: C, 55.43; H, 4.65; N, 9.70. Found C, 55.49; H, 4.68; N, 9.60.

Workup

  1. concentrationthe reaction was concentrated in vacuo until most of the ethanol
  2. customwas removed
  3. washwashed with saturated NaCl
  4. dry with materialThe organic layer was dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-c241851f87f04ef1ad97a260e78b2319
Source dataset
uspto-grants-2002_07
Patent number
US06420426B1

Reaction notes

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