Hydrochloric Acid → 2-(2-Tetrahydropyranyl)oxy-2-(2-mesylamino-1,3-thiazol-4-yl)acetic acid
Reaction equation
[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][CH:8]([C:14]1[N:15]=[C:16]([NH:19][S:20]([CH3:23])(=[O:22])=[O:21])[S:17][CH:18]=1)[C:9]([O:11]CC)=[O:10].[OH-].[Na+].O.Cl>C(OCC)(=O)C>[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][CH:8]([C:14]1[N:15]=[C:16]([NH:19][S:20]([CH3:23])(=[O:21])=[O:22])[S:17][CH:18]=1)[C:9]([OH:11])=[O:10]Participants
Reactant 5
Product 1
Reagents, catalysts & solvents 1
Procedure
To ethyl 2-(2-tetrahydropyranyl)oxy-2-(2-mesylamino-1,3-thiazol-4-yl)acetate, which can be represented as ethyl 2-(2-tetrahydropyranyl)oxy-2-(2-mesylimino-2,3-dihydro-1,3-thiazol-4-yl)acetate, (0.85 g.) was added 1 H sodium hydroxide aqueous solution prepared by sodium hydroxide (0.28 g.) and water (7 ml.), and then the mixture was stirred for 1 hour at room temperature. After the reaction, to the reaction mixture was added ethyl acetate. The mixture was adjusted to pH 1 to 2 with 2 N hydrochloric acid, and the aqueous layer was separated. The aqueous layer was subjected to salting-out and then extracted with ethyl acetate. The extract was washed with a saturated aqueous solution of sodium chloride, dried over magnesium sulfate and then the solvent was distilled off to give a foamy substance of 2-(2-tetrahydropyranyl)oxy-2-(2-mesylamino-1,3-thiazol-4-yl)acetic acid, which can be represented as 2-(2-tetrahydropyranyl)oxy-2-(2-mesylimino-2,3-dihydro-1,3-thiazol-4-yl)acetic acid, (0.52 g.).
Workup
- customAfter the reaction
- customthe aqueous layer was separated
- extractionextracted with ethyl acetate
- washThe extract was washed with a saturated aqueous solution of sodium chloride
- dry with materialdried over magnesium sulfate
- distillationthe solvent was distilled off
Sources & evidence
- ORD record
- ord-b76d2b46c0fe441d8a4d12f05b5bb4b8
- Source dataset
- uspto-grants-1984_04
- Patent number
- US04440766
Reaction notes
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