Hydrochloric Acid → (RS)-[2,6-difluoro-4-(4-methoxy-phenoxy)-phenyl]-ethoxy-acetic acid

HRID 1247371Notes

Reaction equation

C([O:3][C:4](=[O:26])[CH:5]([C:9]1[C:14]([F:15])=[CH:13][C:12]([O:16][C:17]2[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][CH:18]=2)=[CH:11][C:10]=1[F:25])[O:6][CH2:7][CH3:8])C.CO.O[Li].O.Cl>C1COCC1.O.CC(OC)(C)C>[F:15][C:14]1[CH:13]=[C:12]([O:16][C:17]2[CH:18]=[CH:19][C:20]([O:23][CH3:24])=[CH:21][CH:22]=2)[CH:11]=[C:10]([F:25])[C:9]=1[CH:5]([O:6][CH2:7][CH3:8])[C:4]([OH:26])=[O:3]

Participants

Conditions

Temperature: 60 °C

Procedure

(RS)-[2,6-Difluoro-4-(4-methoxy-phenoxy)-phenyl]-ethoxy-acetic acid ethyl ester (455 mg) was dissolved in THF (2.4 ml), MeOH (2.4 ml) and H2O (1.0 ml) and LiOH.H2O (104 mg) was added. The reaction mixture was stirred 1 h at 60° C. The solution was diluted with cold H2O (15 ml) and TBME (15 ml) and acidified with 1 N HCl. The aqueous layer was extracted with two more portions of TBME (15 ml). The combined organic layers were dried (MgSO4) and the solvent was evaporated to obtain 398 mg (95%) of (RS)-[2,6-difluoro-4-(4-methoxy-phenoxy)-phenyl]-ethoxy-acetic acid. White waxy solid. MS 336.9 ([M−H]−).

Workup

extractionThe aqueous layer was extracted with two more portions of TBME (15 ml)
dry with materialThe combined organic layers were dried (MgSO4)
customthe solvent was evaporated

Sources & evidence

ORD record: ord-6462af5322ac40f6ba3f76e8e9e600d2
Source dataset: uspto-grants-2006_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07129238B2

Reaction notes

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