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Hydrochloric Acid → HCID 140357028、化合物

HRID 1109349
ノート
印刷プレビュー

反応式

HRID 1109349 の反応式
C([O:4][C:5]1[CH:6]=[C:7]([S:15](Cl)(=[O:17])=[O:16])[CH:8]=[CH:9][C:10]=1[O:11]C(=O)C)(=O)C.[NH2:19][CH2:20][CH2:21][O:22]/[N:23]=[C:24](/[C:30]1[N:31]=[C:32]([NH:35]C(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[S:33][CH:34]=1)\[C:25]([O:27]CC)=[O:26].[OH-].[Na+].Cl>CN(C)C1C=CN=CC=1.CN(C)C=O.O>[OH:4][C:5]1[CH:6]=[C:7]([S:15]([NH:19][CH2:20][CH2:21][O:22]/[N:23]=[C:24](/[C:30]2[N:31]=[C:32]([NH2:35])[S:33][CH:34]=2)\[C:25]([OH:27])=[O:26])(=[O:16])=[O:17])[CH:8]=[CH:9][C:10]=1[OH:11]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

8

反応物 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 190224303,4-Diacetoxy-benzenesulphonyl chlorideHCID 154041583HCID 154041583、化合物

生成物 1

HCID 140357028HCID 140357028、化合物

試薬・触媒・溶媒 3

HCID 142844-(Dimethylamino)pyridine触媒
HCID 962
Water
溶媒
HCID 6228Dimethylformamide溶媒

反応条件

温度
20 °C

実験手順

1.17 g of 3,4-diacetoxy-benzenesulphonyl chloride were added to a solution of 6.0 g of 2-(tritylamino)-4-thiazoleglyoxylic acid ethyl ester (Z)-O-(2-aminoethyl) oxime and 0.49 g of 4-dimethylamino-pyridine in 50 ml of N,N-dimethylformamide. The reaction solution was stirred at 20° C. for 3 hours, 10 ml of 2N sodium hydroxide solution were then added, and the solution was stirred at 20° C. for an additional hour. Then, 20 ml of water were added and the pH of the reaction mixture was lowered to 3 by the addition of 3N hydrochloric acid. The resulting precipitate was filtered off under suction, washed with a small amount of water and then heated to 50° C. for 40 minutes in 60 ml of 80% aqueous acetic acid. The mixture was cooled to 20° C. and evaporated completely in a vacuum. The residue was dissolved in 30 ml of methanol and treated in an ice bath with a total of 180 ml of diethyl ether. The precipitate was filtered off under suction, suspended in a small amount of water and brought into solution by the dropwise addition of 2N sodium hydroxide solution. The solution of pH 7.5 was applied to a MCI gel column (CHP2OP) conditioned with 1% aqeuous acetic acid and chromatographed according to the procedure described in the first paragraph of this Example. The product was eluted with a 9:1 (v/v) water/acetonitrile mixture. The pure fractions were concentrated completely in a vacuum and the solid residue was crystallized from methanol/diethyl ether. There was obtained 2-amino-4-thiazoleglyoxylic acid (Z)-O-[2-[(3,4-dihydroxyphenyl)sulphonamido]ethyl] oxime as white crystals of melting point 92-94° C. (decomposition).

後処理

  1. stirringthe solution was stirred at 20° C. for an additional hour
  2. filtrationThe resulting precipitate was filtered off under suction
  3. washwashed with a small amount of water
  4. temperatureheated to 50° C. for 40 minutes in 60 ml of 80% aqueous acetic acid
  5. temperatureThe mixture was cooled to 20° C.
  6. customevaporated completely in a vacuum
  7. dissolutionThe residue was dissolved in 30 ml of methanol
  8. additiontreated in an ice bath with a total of 180 ml of diethyl ether
  9. filtrationThe precipitate was filtered off under suction
  10. additionbrought into solution by the dropwise addition of 2N sodium hydroxide solution
  11. customchromatographed
  12. washThe product was eluted with a 9:1 (v/v) water/acetonitrile mixture
  13. concentrationThe pure fractions were concentrated completely in a vacuum
  14. customthe solid residue was crystallized from methanol/diethyl ether

出典と根拠

ORDレコード
ord-e277e62e67534da29118d2f2cb4366d5
出典データセット
uspto-grants-1994_06
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05319140

反応ノート

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