Sodium Hydroxide → HCID 53764372, compound

HRID 2121146Notes

Reaction equation

CO.O.C[O:5][C:6](=[O:36])[C@H:7]([CH2:32][CH2:33][S:34][CH3:35])[NH:8][C:9](=[O:31])[C:10]1[CH:15]=[CH:14][C:13]([CH2:16][O:17][C:18]2[CH:19]=[N:20][CH:21]=[CH:22][CH:23]=2)=[CH:12][C:11]=1[O:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.[OH-].[Na+]>O>[N:20]1[CH:21]=[CH:22][CH:23]=[C:18]([O:17][CH2:16][C:13]2[CH:14]=[CH:15][C:10]([C:9]([NH:8][C@H:7]([C:6]([OH:36])=[O:5])[CH2:32][CH2:33][S:34][CH3:35])=[O:31])=[C:11]([O:24][C:25]3[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=3)[CH:12]=2)[CH:19]=1

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution in 5:1 methanol-H2O (3.5 mL) of [4-(3-pyridyloxymethyl)-2-phenoxybenzoyl]methionine methyl ester (440 mg), prepared as in Example 157G, was added a solution of 50% NaOH (354 mg) in water (0.8 mL) and the reaction mixture was heated at 60° C. for 15 minutes. The reaction mixture was concentrated in vacuo and the residue was taken up in H2O (3, mL). The aqueous solution was acidified with concentrated HCl (415 mg) and 2 drops of ethyl acetate were added. The resulting solid was filtered and dried in a vacuum oven at 60° C. for 3 hours to give [4-(3-pyridyloxymethyl)-2-phenoxybenzoyl]methionine (373 mg). mp 195° C.; 1H NMR (300 MHz, DMSO-d6) δ 1.90 (m, 4H), 2.37 (m, 2H), 4.44 (m, 1H), 5.20 (s, 2H), 7.01 (s, 2H), 7.04 (s, 1H), 7.16 (t, 1H, J=7.4 Hz), 3.66 (m, 5H), 7.70 (d, 1H, J=9.0 Hz), 8.17 (dd, 1H, J=4.4, 1.5 Hz), 8.30 (d, 1H, J=3 Hz). Anal calcd for C24H24N2O5S: C, 63.70; H, 5.35; N, 6:59. Found: C, 63.46; H, 5.11; N, 6.08.

Workup

concentrationThe reaction mixture was concentrated in vacuo
additionwere added
filtrationThe resulting solid was filtered
customdried in a vacuum oven at 60° C. for 3 hours

Sources & evidence

ORD record: ord-36d683e5c1fa428682351c7646a60c21
Source dataset: uspto-grants-2004_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06693123B2

Reaction notes

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