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

HRID 69560

反応式

HRID 69560 の反応式
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]

参加物

5

反応物 3

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

生成物 1

HCID 67116892{2-[(tert-butoxycarbonyl)imino]-5-(methoxymethyl)-1,3,4-thiadiazol-3(2H)-yl}acetic acid収率 89.8%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
60 °C

実験手順

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 a31 (360 g, 1.468 mol, 1 eq) in tetrahydrofurane (3 l) at room temperature. Sodium hydride (52.83 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. for the night, 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 Na2S2O3 (to remove the coloration of iodine) and evaporated to dryness to furnish 455.7 g of {2-[(tert-butoxycarbonyl)imino]-5-(methoxymethyl)-1,3,4-thiadiazol-3(2H)-yl}acetic acid a33 which is used directly in the next step without any further purification.

後処理

  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 Na2S2O3 (
  5. customto remove the coloration of iodine) and
  6. customevaporated to dryness

出典と根拠

ORDレコード
ord-0f53db14562843d99ed393f961dd7ad2
出典データセット
uspto-grants-2014_09
特許番号
US08822508B2

関連ノート

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