Hydrochloric Acid → HCID 58697770, compound

HRID 1172662Notes

Reaction equation

[CH3:1][C:2]1[N:3]=[C:4]([C:22]2[CH:27]=[CH:26][C:25]([C:28]([F:31])([F:30])[F:29])=[CH:24][CH:23]=2)[S:5][C:6]=1[C@H:7]([O:10]C(=O)[C@H](OC)C1C=CC=CC=1)[CH2:8][CH3:9].[OH-].[Na+].Cl>O1CCCC1.C(O)C.O>[CH3:1][C:2]1[N:3]=[C:4]([C:22]2[CH:27]=[CH:26][C:25]([C:28]([F:31])([F:29])[F:30])=[CH:24][CH:23]=2)[S:5][C:6]=1[C@H:7]([OH:10])[CH2:8][CH3:9]

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of 3.74 g of (−)-(R)-methoxy-phenyl-acetic acid (R)-1-[4-methyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-yl]-propyl ester in 19 mL of tetrahydrofuran and 19 mL of ethanol at 0° C. was dropwise added 24.5 mL of a molar solution of sodium hydroxide in 20.4 mL of water. The resulting mixture was stirred at 0° C. for 15 minutes then 24.5 mL of a 5N solution of hydrochloric acid in 20.4 mL of water was added. After removal of the organic solvents under vacuum, the mixture was extracted with ethyl acetate, filtered through a silicone treated paper filter and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (dichloromethane 90/ethyl acetate 10) to give 2.09 g of (+)-(R)-1-[4-methyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-yl]-propan-1-ol.

Workup

customat 0° C.
customAfter removal of the organic solvents under vacuum
extractionthe mixture was extracted with ethyl acetate
filtrationfiltered through a silicone treated paper
filtrationfilter
concentrationconcentrated under reduced pressure
customThe residue was purified by column chromatography on silica gel (dichloromethane 90/ethyl acetate 10)

Sources & evidence

ORD record: ord-6cf81ea8f0b642739c644d8cad2c15e1
Source dataset: uspto-grants-2010_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07834030B2

Reaction notes

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