Hydrochloric Acid → 2-[(Z)-[1-(5-amino-1,2,4-thiadiazol-3-yl)-2-methylsulfonyloxy-2-oxoethylidene]amino]oxy-2-methylpropanoic acid

HRID 1031208ノート

反応式

HRID 1031208 の反応式
[NH2:1][C:2]1[S:6][N:5]=[C:4](/[C:7](=[N:11]/[O:12][C:13]([C:16]([OH:18])=[O:17])([CH3:15])[CH3:14])/[C:8]([OH:10])=[O:9])[N:3]=1.[CH3:19][S:20](Cl)(=[O:22])=[O:21].C(=O)(O)[O-].[K+].Cl>CN(C)C(=O)C.C(OCC)(=O)C.O>[NH2:1][C:2]1[S:6][N:5]=[C:4](/[C:7](=[N:11]/[O:12][C:13]([C:16]([OH:18])=[O:17])([CH3:15])[CH3:14])/[C:8]([O:10][S:20]([CH3:19])(=[O:22])=[O:21])=[O:9])[N:3]=1

参加物

8

反応物 4

HCID 313Hydrochloric AcidHCID 31297Methanesulfonyl chlorideHCID 516893Potassium BicarbonateHCID 15077653(Z)-2-((((5-Amino-1,2,4-thiadiazol-3-yl)(carboxy)methylene)amino)oxy)-2-methylpropanoic acid

生成物 1

HCID 879472882-[(Z)-[1-(5-amino-1,2,4-thiadiazol-3-yl)-2-methylsulfonyloxy-2-oxoethylidene]amino]oxy-2-methylpropanoic acid収率 31.2%

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 8857Ethyl Acetate溶媒HCID 31374Dimethylacetamide溶媒

反応条件

温度
5 °C

実験手順

To a solution of (Z)-2-(5-amino-1,2,4-thiadiazol-3-yl)-2-(1-carboxy-1-methylethoxyimino)acetic acid (2.74 g) in N,N-dimethylacetamide (45 ml) were added methanesulfonyl chloride (1.15 g) and potassium bicarbonate (1.20 g) under cooling in an ice bath. The mixture was stirred for 2.5 hours at 5° C. and poured into a cold mixture of water (200 ml), ethyl acetate (200 ml) and 1N hydrochloric acid (6 ml). The mixture was stirred for 5 minutes under cooling in an ice bath. The organic layer was separated, washed with cold water (200ml×2) and with a cold saturated aqueous solution of sodium chloride, dried over magnesium sulfate and evaporated. Toluene was added to the residue. To the mixture was added methylene chloride and the mixture was cooled for 10 minutes in an ice bath. The crystals were collected by filtration, washed with methylene chloride and air-dried to give methanesulfonyl (Z)-2-(5-amino-1,2,4-thiadiazol-3-yl)-2-(1-carboxy-1-methylethoxyimino)acetate (1.1 g).

後処理

  1. temperatureunder cooling in an ice bath
  2. stirringThe mixture was stirred for 5 minutes
  3. temperatureunder cooling in an ice bath
  4. customThe organic layer was separated
  5. washwashed with cold water (200ml×2) and with a cold saturated aqueous solution of sodium chloride
  6. dry with materialdried over magnesium sulfate
  7. customevaporated
  8. additionToluene was added to the residue
  9. additionTo the mixture was added methylene chloride
  10. temperaturethe mixture was cooled for 10 minutes in an ice bath
  11. filtrationThe crystals were collected by filtration
  12. washwashed with methylene chloride
  13. customair-dried

出典と根拠

ORDレコード
ord-74b493f0c9b64b68b062d39c82d0f46d
出典データセット
uspto-grants-1992_04
特許番号
US05108997

反応ノート

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