Sodium borohydride → Ethyl 2-hydroxy-2-(2-mesylamino-1,3-thiazol-4-yl)acetate

HRID 1659389Notes

Reaction equation

HRID 1659389 reaction equation
[S:1]([NH:5][C:6]1[S:7][CH:8]=[C:9]([C:11](=[O:17])[C:12]([O:14][CH2:15][CH3:16])=[O:13])[N:10]=1)([CH3:4])(=[O:3])=[O:2].[BH4-].[Na+]>C(O)C>[OH:17][CH:11]([C:9]1[N:10]=[C:6]([NH:5][S:1]([CH3:4])(=[O:2])=[O:3])[S:7][CH:8]=1)[C:12]([O:14][CH2:15][CH3:16])=[O:13]

Participants

5

Reactant 3

HCID 4311764Sodium borohydrideHCID 19978726Ethyl 2-(2-mesylamino-1,3-thiazol-4-yl)glyoxylateHCID 178473045HCID 178473045, compound

Product 1

HCID 20254378Ethyl 2-hydroxy-2-(2-mesylamino-1,3-thiazol-4-yl)acetate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a mixture of ethyl 2-(2-mesylamino-1,3-thiazol-4-yl)glyoxylate, which can be represented as ethyl 2-(2-mesylimino-2,3-dihydro-1,3-thiazol-4-yl)glyoxylate, (3.60 g.) and ethanol (50 ml.) was added sodium borohydride (0.32 g.) under stirring and ice-cooling, and then the mixture was stirred for 40 minutes at room temperature. After the reaction, the reaction mixture was concentrated. The residue was poured into a mixture of ethyl acetate (100 ml.) and dilute hydrochloric acid, and the aqueous solution was separated. Thus obtained aqueous solution (pH 1 to 2) was subjected to salting-out and then extracted with ethyl acetate. The extract was washed with a saturated aqueous solution of sodium chloride and dried over magnesium sulfate. The extract was treated with activated charcoal and then the solvent was distilled off to give a solid 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, (2.6 g.)

Workup

  1. temperatureice-cooling
  2. stirringthe mixture was stirred for 40 minutes at room temperature
  3. customAfter the reaction
  4. concentrationthe reaction mixture was concentrated
  5. additionThe residue was poured into a mixture of ethyl acetate (100 ml.) and dilute hydrochloric acid
  6. customthe aqueous solution was separated
  7. extractionextracted with ethyl acetate
  8. washThe extract was washed with a saturated aqueous solution of sodium chloride
  9. dry with materialdried over magnesium sulfate
  10. additionThe extract was treated with activated charcoal
  11. distillationthe solvent was distilled off

Sources & evidence

ORD record
ord-be67a4da8a2641839be3fb912af1f2d8
Source dataset
uspto-grants-1981_12
Patent number
US04303655

Reaction notes

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