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Sodium Iodide → t-Butyl 2-(2-amino-4-thiazolyl)-2-[[(p-nitrobenzyloxycarbonyl)methoxy]imino]-acetate

HRID 256095
ノート
印刷プレビュー

反応式

HRID 256095 の反応式
[C:1]([O:5][C:6](=[O:16])/[C:7](/[C:10]1[N:11]=[C:12]([NH2:15])[S:13][CH:14]=1)=[N:8]\[OH:9])([CH3:4])([CH3:3])[CH3:2].Br[CH2:18][C:19]([O:21][CH2:22][C:23]1[CH:28]=[CH:27][C:26]([N+:29]([O-:31])=[O:30])=[CH:25][CH:24]=1)=[O:20].C(N(C(C)C)C(C)C)C.[I-].[Na+]>C(#N)C>[C:1]([O:5][C:6](=[O:16])[C:7]([C:10]1[N:11]=[C:12]([NH2:15])[S:13][CH:14]=1)=[N:8][O:9][CH2:18][C:19]([O:21][CH2:22][C:23]1[CH:28]=[CH:27][C:26]([N+:29]([O-:31])=[O:30])=[CH:25][CH:24]=1)=[O:20])([CH3:4])([CH3:2])[CH3:3]
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 5238Sodium IodideHCID 81531DiisopropylethylamineHCID 70153214-Nitrobenzyl bromoacetateHCID 13826576tert-butyl 2-(2-amino-1,3-thiazol-4-yl)-2-(N-hydroxyimino)acetate

生成物 1

HCID 53971680t-Butyl 2-(2-amino-4-thiazolyl)-2-[[(p-nitrobenzyloxycarbonyl)methoxy]imino]-acetate収率 75.2%

試薬・触媒・溶媒 1

HCID 6342
Acetonitrile
溶媒

実験手順

6.1 g (25 mmol) of 2-(2-amino-4-thiazolyl)-2-(Z)-hydroxyimino-acetic acid t-butyl ester are dispersed in 250 ml of dry acetonitrile. There are now added thereto at room temperature while stirring 13.7 g (50 mmol) of 4-nitrobenzyl bromoacetate and 12.9 ml (75 mmol) of N-ethyldiisopropylamine. 5 minutes later 7.5 g (50 mmol) of sodium iodide are added thereto. The mixture is stirred at room temperature for 3.5 hours in an argon atmosphere. The solvent is subsequently removed by evaporation and the residue is diluted with 500 ml of ethyl acetate. The resulting solution is washed four times with a total of 2 l of water. The water is extracted with 300 ml of ethyl acetate and the combined ethyl acetate solutions are dried over sodium sulphate and evaporated to dryness. After crystallization from ethyl acetate/hexane, there are obtained 8.2 g (75%) of 2-(2-amino-4-thiazolyl)-2-[[(p-nitrobenzyloxycarbonyl)methoxy]imino]-acetic acid t-butyl ester of melting point 146.8° (decomposition).

後処理

  1. additionThere are now added
  2. customThe solvent is subsequently removed by evaporation
  3. additionthe residue is diluted with 500 ml of ethyl acetate
  4. washThe resulting solution is washed four times with a total of 2 l of water
  5. extractionThe water is extracted with 300 ml of ethyl acetate
  6. dry with materialthe combined ethyl acetate solutions are dried over sodium sulphate
  7. customevaporated to dryness
  8. customAfter crystallization from ethyl acetate/hexane, there

出典と根拠

ORDレコード
ord-71b16a2e4266421e8ee31770ae5cfa13
出典データセット
uspto-grants-1987_10
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US04699986

反応ノート

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