Iodine → Ethyl 2-amino-2-cyanoacetate

HRID 131358

반응식

HRID 131358 반응식
C(=O)(O)[O-].[Na+].[C:6]([C:8](=[N:14]O)[C:9]([O:11][CH2:12][CH3:13])=[O:10])#[N:7].S(S([O-])=O)([O-])=O.[Na+].[Na+].II>CCOC(C)=O.O>[CH2:12]([O:11][C:9](=[O:10])[CH:8]([NH2:14])[C:6]#[N:7])[CH3:13]

참가 물질

7

반응물 4

HCID 807IodineHCID 24489Sodium DithioniteHCID 516892Sodium BicarbonateHCID 6399078Ethyl 2-cyano-2-(hydroxyimino)acetate

생성물 1

HCID 288716Ethyl 2-amino-2-cyanoacetate수율 31%

시약·촉매·용매 2

HCID 962Water용매HCID 8857Ethyl Acetate용매

실험 절차

Dilute aqueous saturated sodium bicarbonate (560 mL) with deionized water (700 mL). and stir the solution while addinng ethyl cyanoglyoxylate-2-oxime (70.0 g, 493 mmol), in portions (note: some off-gassing and a gentle endotherm were observed). Add sodium dithionite (238 g, 1.37 mol, 2.8 eq.) in portions and stir at rt. After 2.5-3 hours, during this time the reaction was monitored by TLC (EtOAc, I2 stain), saturate the solution with sodium chloride (400 g), and extract the product CH2Cl2 (1×500 mL, 3×250 mL), making sure solid NaCl was visible (more added if necessary) during the extractions. Combine the organic layers, dry over (MgSO4), filter, and concentrate the filtrate to dryness in vacuo on a rotovapor at low bath temperature (30-35° C.) to afford 19.6 g (31%) crude amino-cyano-acetic acid ethyl ester which was used immediately in the next reaction.

후처리

  1. concentrationsaturate the solution with sodium chloride (400 g)
  2. extractionextract the product CH2Cl2 (1×500 mL, 3×250 mL)
  3. additionmore added if necessary)
  4. extractionduring the extractions
  5. dry with materialCombine the organic layers, dry over (MgSO4)
  6. filtrationfilter
  7. concentrationconcentrate the filtrate to dryness in vacuo on a rotovapor at low bath temperature (30-35° C.)

출처 및 근거

ORD 기록
ord-50c99a4e5c7647ccb3b751273d252372
출처 데이터셋
uspto-grants-2008_06
특허 번호
US07384934B2

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