Sodium Hydroxide → [5-(6-Morpholin-4-yl-4-oxo-4h-pyran-2-yl)-9h-thioxanthen-2-yloxy]-acetic acid sodium salt

HRID 33812Notes

Reaction equation

C[O:2][C:3](=[O:33])[CH2:4][O:5][C:6]1[CH:19]=[CH:18][C:17]2[S:16][C:15]3[C:10](=[CH:11][CH:12]=[CH:13][C:14]=3[C:20]3[O:21][C:22]([N:27]4[CH2:32][CH2:31][O:30][CH2:29][CH2:28]4)=[CH:23][C:24](=[O:26])[CH:25]=3)[CH2:9][C:8]=2[CH:7]=1.[OH-].[Na+:35]>C1COCC1>[Na+:35].[N:27]1([C:22]2[O:21][C:20]([C:14]3[CH:13]=[CH:12][CH:11]=[C:10]4[C:15]=3[S:16][C:17]3[CH:18]=[CH:19][C:6]([O:5][CH2:4][C:3]([O-:33])=[O:2])=[CH:7][C:8]=3[CH2:9]4)=[CH:25][C:24](=[O:26])[CH:23]=2)[CH2:32][CH2:31][O:30][CH2:29][CH2:28]1

Participants

Conditions

Temperature: 40 °C

Procedure

To a solution of [5-(6-Morpholin-4-yl-4-oxo-4H-pyran-2-yl)-9H-thioxanthen-2-yloxy]-acetic acid methyl ester (1.02 g, 2.18 mmol) in THF (25 ml) was added aqueous NaOH (2.4 ml, 2.4 mmol, 1M solution). The mixture was stirred at 40° C. for 2 hours whereupon it was cooled to room temperature and concentrated in vacuo to give a brown oil. The residue was azeotroped with toluene (3×10 ml) to give the title compound as a fine, dark brown powder that was used without further purification (1.03 g, 100%), m/z (LC-MS, ESP), RT=3.72 min, (M++1)-Na+=452

Workup

temperaturewas cooled to room temperature
concentrationconcentrated in vacuo
customto give a brown oil
customThe residue was azeotroped with toluene (3×10 ml)

Sources & evidence

ORD record: ord-081d8fc791624b8792950efbcc57a30a
Source dataset: uspto-grants-2008_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07429660B2

Reaction notes

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