p-Toluenesulfonic acid → Ethyl 2-(2-tetrahydropyranyl)oxy-2-(2-mesylamino-1,3-thiazol-4-yl)acetate

HRID 638425Notes

Reaction equation

HRID 638425 reaction equation
[OH:1][CH:2]([C:8]1[N:9]=[C:10]([NH:13][S:14]([CH3:17])(=[O:16])=[O:15])[S:11][CH:12]=1)[C:3]([O:5][CH2:6][CH3:7])=[O:4].[O:18]1[CH:23]=[CH:22][CH2:21][CH2:20][CH2:19]1.C1(C)C=CC(S(O)(=O)=O)=CC=1.C(=O)(O)[O-].[Na+]>C(OCC)(=O)C>[O:18]1[CH2:23][CH2:22][CH2:21][CH2:20][CH:19]1[O:1][CH:2]([C:8]1[N:9]=[C:10]([NH:13][S:14]([CH3:17])(=[O:15])=[O:16])[S:11][CH:12]=1)[C:3]([O:5][CH2:6][CH3:7])=[O:4]

Participants

7

Reactant 5

HCID 6101p-Toluenesulfonic acidHCID 80803,4-dihydro-2H-pyranHCID 516892Sodium BicarbonateHCID 20254378Ethyl 2-hydroxy-2-(2-mesylamino-1,3-thiazol-4-yl)acetateHCID 178473046HCID 178473046, compound

Product 1

HCID 20254379Ethyl 2-(2-tetrahydropyranyl)oxy-2-(2-mesylamino-1,3-thiazol-4-yl)acetate

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a suspension of ethyl 2-hydroxy-2-(2-mesylamino-1,3-thiazol-4-yl)acetate, which can be represented as ethyl 2-hydroxy-2-(2-mesylimino-2,3-dihydro-1,3-thiazol-4-yl)acetate, (1.0 g.) and 3,4-dihydro-2H-pyran (0.36 g.) in ethyl acetate (5 ml.) was added p-toluene sulfonic acid (10 mg) at room temperature with stirring, and then the suspension was stirred for 8 hours at the same temperature. After the reaction, the reaction mixture was poured into 5% sodium bicarbonate aqueous solution (10 ml.) and then the aqueous layer was separated. To the remaining organic layer was added diethyl ether (10 ml.) and then extracted with 5% sodium bicarbonate aqueous solution (20 ml.). Thus obtained aqueous extract was combined with the separated aqueous layer and adjusted to pH 4 with acetic acid and then extracted with ethyl acetate. The extract was washed with a saturated aqueous solution of sodium chloride, treated with activated charcoal and then dried over magnesium sulfate. The solvent was distilled off from the extract to give dark yellow oil of 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, (1.0 g.).

Workup

  1. stirringthe suspension was stirred for 8 hours at the same temperature
  2. customAfter the reaction
  3. customthe aqueous layer was separated
  4. additionTo the remaining organic layer was added diethyl ether (10 ml.)
  5. extractionextracted with 5% sodium bicarbonate aqueous solution (20 ml.)
  6. extractionThus obtained aqueous extract
  7. extractionextracted with ethyl acetate
  8. washThe extract was washed with a saturated aqueous solution of sodium chloride
  9. additiontreated with activated charcoal
  10. dry with materialdried over magnesium sulfate
  11. distillationThe solvent was distilled off from the
  12. extractionextract

Sources & evidence

ORD record
ord-e24b59a0a8474ea8ad461434525a6ef8
Source dataset
uspto-grants-1985_12
Patent number
US04560765

Reaction notes

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