Iodoacetic Acid → {2-[(tert-butoxycarbonyl)imino]-5-(methoxymethyl)-1,3,4-thiadiazol-3(2H)-yl}acetic acid

HRID 1851714

반응식

HRID 1851714 반응식
I[CH2:2][C:3]([OH:5])=[O:4].[CH3:6][O:7][CH2:8][C:9]1[S:13][C:12]([NH:14][C:15](=[O:21])[O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[N:11][N:10]=1.[H-].[Na+]>O1CCCC1>[C:17]([O:16][C:15]([N:14]=[C:12]1[N:11]([CH2:2][C:3]([OH:5])=[O:4])[N:10]=[C:9]([CH2:8][O:7][CH3:6])[S:13]1)=[O:21])([CH3:20])([CH3:19])[CH3:18]

참가 물질

5

반응물 3

HCID 5240Iodoacetic AcidHCID 24758Sodium hydrideHCID 84382575Tert-butyl [5-(methoxymethyl)-1,3,4-thiadiazol-2-yl]carbamate

생성물 1

HCID 67116892{2-[(tert-butoxycarbonyl)imino]-5-(methoxymethyl)-1,3,4-thiadiazol-3(2H)-yl}acetic acid수율 90%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
60 °C

실험 절차

Iodoacetic acid (409.3 g, 2.2 mol, 1.5 eq) is added in one portion to a solution of tert-butyl [5-(methoxymethyl)-1,3,4-thiadiazol-2-yl]carbamate a13 (360 g, 1.47 mol, 1 eq) in tetrahydrofurane (3 l) at room temperature. Sodium hydride (52.8 g, 2.2 mol, 1.5 eq) is then added portionwise, in 30 minutes, at room temperature. The reaction mixture is heated at 60° C. overnight, and the solvent is evaporated under reduced pressure. Water is added to the residue, the solution is acidified to pH=2 with aqueous 6N HCl, then extracted with CH2Cl2. The organic layer is washed with 10% aqueous sodium thiosulfate and evaporated to dryness to afford 455.7 g of {2-[(tert-butoxy-carbonyl)imino]-5-(methoxymethyl)-1,3,4-thiadiazol-3(2H)-yl}acetic acid a14 which is used directly in the next step without any further purification.

후처리

  1. customthe solvent is evaporated under reduced pressure
  2. additionWater is added to the residue
  3. extractionextracted with CH2Cl2
  4. washThe organic layer is washed with 10% aqueous sodium thiosulfate
  5. customevaporated to dryness

출처 및 근거

ORD 기록
ord-a5c89827bc5643c2a4dbdcb84fa5fb1c
출처 데이터셋
uspto-grants-2015_02
특허 번호
US08957218B2

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