Lithium hydroxide, monohydrate → [4-(3-Pyridylcarbonylamino)-2-(2-methylphenyl)benzoyl]methionine

HRID 2121230Notes

Reaction equation

HRID 2121230 reaction equation
C[O:2][C:3](=[O:34])[C@H:4]([CH2:30][CH2:31][S:32][CH3:33])[NH:5][C:6](=[O:29])[C:7]1[CH:12]=[CH:11][C:10]([NH:13][C:14]([C:16]2[CH:17]=[N:18][CH:19]=[CH:20][CH:21]=2)=[O:15])=[CH:9][C:8]=1[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=1[CH3:28].O[Li].O>C1COCC1.O>[N:18]1[CH:19]=[CH:20][CH:21]=[C:16]([C:14]([NH:13][C:10]2[CH:11]=[CH:12][C:7]([C:6]([NH:5][C@H:4]([C:3]([OH:34])=[O:2])[CH2:30][CH2:31][S:32][CH3:33])=[O:29])=[C:8]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=3[CH3:28])[CH:9]=2)=[O:15])[CH:17]=1

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 59926755[4-(3-Pyridylcarbonylamino)-2-(2-methylphenyl)benzoyl]methionine Methyl Ester

Product 1

HCID 10766525[4-(3-Pyridylcarbonylamino)-2-(2-methylphenyl)benzoyl]methionineYield 64.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of the product of Example 300 (140 mg, 0.29 mmol) in THF (6 mL) was added a solution of LiOH.H2O (37 mg, 88 mmol) in H2O (1 mL) and the resulting solution stirred for 2 hours at ambient temperature. The reaction was concentrated in vacuo and 1 N HCl was added to the residue. The resulting precipitate was filtered and washed with H2O. Lyopholization gave the title compound (87 mg, 59%) as a white powder. 1H NMR (300 MHz, DMSO-d6, 90° C.) δ 9.12 (d, 1H, J=2.4 Hz), 8.74 (dd, 1H, J=4.9, 1.9 Hz), 8.31 (dt, 1H, J=7.9, 1.8 Hz), 7.84 (dd, 1H, J=7.9, 1.8 Hz), 7.63 (s, 1H), 7.61 (d, 1H, J=2.4 Hz), 7.54 (dd, 1H, J=7.9, 4.9 Hz), 7.45 (d, 1H, J=7.9 Hz), 7.23-7.21 (m, 2H), 7.19-7.15 (m, 2H), 4.30-4.26 (m, 1H), 2.28-2.22 (m, 1H), 2.20-2.14 (m, 1H), 2.11 (s, 3H), 1.98 (s, 3H), 1.88-1.81 (m, 1H), 1.75-1.68 (m, 1H), MS m/z 464 (M+1)+, 446. Anal calcd for C25H25N3O4S.HCl.0.5 H2O (509.01): C, 58.99; H, 5.35; N, 8.26. Found: C, 59.38; H, 5.49; N, 7.89.

Workup

  1. concentrationThe reaction was concentrated in vacuo and 1 N HCl
  2. additionwas added to the residue
  3. filtrationThe resulting precipitate was filtered
  4. washwashed with H2O

Sources & evidence

ORD record
ord-302a4338c01045699264b41dce205520
Source dataset
uspto-grants-2004_02
Patent number
US06693123B2

Reaction notes

Loading…