Sodium Hydroxide → HCID 22093453, compound

HRID 457990Notes

Reaction equation

HRID 457990 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, extracted 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, 1 H), 8.17 (s, 1 H), 8.09 (dd, J, =8.1 Hz, J2=2.4 Hz, 1 H), 7.78 (d, J=7.5 Hz, 1 H), 7.65–7.52 (m, 2 H), 7.13 (d, J=13.8 Hz, 1 H), 4.85 (s, 2 H), 4.62 (d, J=6 Hz, 2 H), 3.71 (t, J=4.7 Hz, 4 H), 2.91 (t, J=4.8 Hz, 4 H). 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. extractionextracted with ethyl acetate
  4. washwashed with saturated NaCl
  5. dry with materialThe organic layer was dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-df78053e1a3f4f75a8184f99d3bba85f
Source dataset
uspto-grants-2007_03
Patent number
US07189749B2

Reaction notes

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