Potassium methyl N-cyanodithioimidocarbonate → HCID 68540342, 화합물

HRID 1442638

반응식

HRID 1442638 반응식
[C:1]([O:5][C:6](=[O:14])[C:7]([C:12]#[N:13])=[C:8]([OH:11])[CH2:9]Cl)([CH3:4])([CH3:3])[CH3:2].[C:15]([N:17]=[C:18]([S-:21])[S:19][CH3:20])#[N:16].[K+]>CC(C)=O>[C:1]([O:5][C:6](=[O:14])[CH:7]([C:12]#[N:13])[C:8]([C:9]1[S:21][C:18]([S:19][CH3:20])=[N:17][C:15]=1[NH2:16])=[O:11])([CH3:4])([CH3:3])[CH3:2]

참가 물질

4

반응물 2

HCID 2733091Potassium methyl N-cyanodithioimidocarbonateHCID 768375794-Chloro-2-cyano-3-hydroxy-but-2-enoic acid tert-butyl ester

생성물 1

HCID 68540342HCID 68540342, 화합물

시약·촉매·용매 1

HCID 180Acetone용매

실험 절차

To a stirred solution of 4-chloro-2-cyano-3-hydroxy-but-2-enoic acid tert-butyl ester Compound 1c (51.3 g, 236 mmol) at 0° C. in acetone (750 mL) was added potassium methyl N-cyanodithioimidocarbonate Compound 1e (40.2 g, 236 mmol). After 1 hr the reaction was allowed to warm to RT. The reaction mixture was evaporated down after stirring for 18 hrs. The resulting residue was extracted with ethyl acetate from saturated NaHCO3. The combined organic layers were dried over MgSO4 and the solvent removed under reduced pressure to yield a tan foam, 3-(4-amino-2-methylsulfanyl-thiazol-5-yl)-2-cyano-3-oxo-propionic acid tert-butyl ester Compound 1h, 72.2 g. 1H NMR (CDCl3) δ 4.34 (br s, 2H), 3.14 (br s, 1H), 2.70 (br s, 3H), 1.47 (br s, 9H). MS 314 (MH+).

후처리

  1. customThe reaction mixture was evaporated down
  2. extractionThe resulting residue was extracted with ethyl acetate from saturated NaHCO3
  3. dry with materialThe combined organic layers were dried over MgSO4
  4. customthe solvent removed under reduced pressure

출처 및 근거

ORD 기록
ord-8aafb594f24d4c63800e65f8ca8aeeb0
출처 데이터셋
uspto-grants-2010_02
특허 번호
US07659284B2

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