Methanol → Methyl 5-oxo-L-prolinate

HRID 21757

반응식

HRID 21757 반응식
[CH3:1]O.S(Cl)(Cl)(=O)=O.[NH:8]1[C:12](=[O:13])[CH2:11][CH2:10][C@H:9]1[C:14]([OH:16])=[O:15]>CN(C=O)C>[CH3:1][O:15][C:14](=[O:16])[C@@H:9]1[CH2:10][CH2:11][C:12](=[O:13])[NH:8]1

참가 물질

5

반응물 3

HCID 887MethanolHCID 7405L-Pyroglutamic AcidHCID 24648Sulfuryl chloride

생성물 1

HCID 78646Methyl 5-oxo-L-prolinate수율 91%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To methanol (30.0 mL), cooled to -10° to -15° C., was slowly added sulfuryl chloride (11.0 mL, 178 mmol), DMF (0.133 mL) and L-pyroglutamic acid (L=(S) configuration, 10.0 g, 77.5 mmol, Sigma Chemical Co.). The stirred mixture was allowed to warm slowly and then stirred at room temperature for 36 hours. The methanol was removed under vacuum, and the residue was dissolved in ethyl acetate (400 mL). Water (~10 mL) was added, followed by the addition of sodium carbonate until basic. The organic layer was decanted, the slurry was washed with ethyl acetate (4×15 mL), and the organics were then combined and dried over magnesium sulfate. Removal of the solvent gave crude pyroglutamic methyl ester (10.04 g, 91%). NMR and MS analysis indicated >95% purity.

후처리

  1. temperatureto warm slowly
  2. customThe methanol was removed under vacuum
  3. dissolutionthe residue was dissolved in ethyl acetate (400 mL)
  4. additionWater (~10 mL) was added
  5. additionfollowed by the addition of sodium carbonate until basic
  6. customThe organic layer was decanted
  7. washthe slurry was washed with ethyl acetate (4×15 mL)
  8. dry with materialdried over magnesium sulfate
  9. customRemoval of the solvent

출처 및 근거

ORD 기록
ord-115cf92b46b24353a20ee1534f2265c7
출처 데이터셋
uspto-grants-1995_06
특허 번호
US05424444

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