HCID 86607111, compound → HCID 63946621, compound

HRID 900892Notes

Reaction equation

HRID 900892 reaction equation
C([NH:4][C:5]1[S:6][C:7]([S:11]([N:14]2[CH2:18][CH2:17][CH:16]([OH:19])[CH2:15]2)(=[O:13])=[O:12])=[C:8]([CH3:10])[N:9]=1)(=O)C>Cl>[NH2:4][C:5]1[S:6][C:7]([S:11]([N:14]2[CH2:18][CH2:17][CH:16]([OH:19])[CH2:15]2)(=[O:13])=[O:12])=[C:8]([CH3:10])[N:9]=1

Participants

3

Reactant 1

HCID 86607111HCID 86607111, compound

Product 1

HCID 63946621HCID 63946621, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Conditions

Temperature
80 °C

Procedure

A stirred suspension of (RS)-1-(2-acetamido-4-methyl-thiazole-5-sulfonyl)-pyrrolidin-3-ol (0.82 g, 2.68 mmol) in 6N hydrochloric acid (13 ml) was heated for 2 h at 80° C. evaporated, and saturated NaHCO3 solution (20 ml) was added. The mixture was extracted with ethyl acetate (3×50 ml), the combined organic layers washed with brine (50 ml), dried (MgSO4) and evaporated. The crude product was further purified by crystallization (dichloromethane/MeOH/hexane) to yield the title compound (0.62 g, 88%) as a white solid. MS (ISP) 263.8 [(M+H)+]; mp 165° C.

Workup

  1. customevaporated
  2. additionsaturated NaHCO3 solution (20 ml) was added
  3. extractionThe mixture was extracted with ethyl acetate (3×50 ml)
  4. washthe combined organic layers washed with brine (50 ml)
  5. dry with materialdried (MgSO4)
  6. customevaporated
  7. customThe crude product was further purified by crystallization (dichloromethane/MeOH/hexane)

Sources & evidence

ORD record
ord-6c9d9a89b3804888a3144e1d22dbb112
Source dataset
uspto-grants-2008_04
Patent number
US07361659B2

Reaction notes

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