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Hydrochloric Acid → [(2-tert-Butyl-1,1-dioxido-3-oxo-5-phenyl-2,3-dihydroisothiazol-4-yl)amino]acetic acid

HRID 2421952
ノート
印刷プレビュー

反応式

HRID 2421952 の反応式
[C:1]([N:5]1[C:9](=[O:10])[C:8]([NH:11][CH2:12][C:13]([O:15]C)=[O:14])=[C:7]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[S:6]1(=[O:24])=[O:23])([CH3:4])([CH3:3])[CH3:2].CO.[Li+].[OH-].Cl>O1CCOCC1.O>[C:1]([N:5]1[C:9](=[O:10])[C:8]([NH:11][CH2:12][C:13]([OH:15])=[O:14])=[C:7]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[S:6]1(=[O:24])=[O:23])([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

7

反応物 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 3939Lithium HydroxideHCID 86625868HCID 86625868、化合物

生成物 1

HCID 67241765[(2-tert-Butyl-1,1-dioxido-3-oxo-5-phenyl-2,3-dihydroisothiazol-4-yl)amino]acetic acid収率 41.4%

試薬・触媒・溶媒 2

HCID 962Water
溶媒
HCID 312751,4-Dioxane溶媒

実験手順

Methyl [(2-tert-butyl-1,1-dioxido-3-oxo-5-phenyl-2,3-dihydroisothiazol-4-yl)amino]acetate (1.28 g, 3.64 mmol) was dispersed in a mixture of dioxane (20 mL), MeOH (20 mL) and water (20 mL). Aqueous LiOH (1M, 0.218 g, 9.10 mmol) was added and the reaction mixture was stirred at rt for 2 h. Aqueous HCl was carefully added to the reaction mixture to give the pH˜1 and the resulting mixture was extracted with DCM. The organic phases were combined, dried over Na2SO4, filtered, evaporated and the crude residue was purified by preparative HPLC giving the title compound (0.51 g, 41%). 1H-NMR (CD3OD, 500 MHz): δ 7.52-7.48 (m, 2H), 7.46-7.42 (m, 3H), 5.41 (brs, 8H) 1.95 (s, 2H), 1.71 (s, 9H); 13C-NMR (CD3OD, 125 MHz): δ 178.4, 174.8, 160.8, 136.5, 132.8, 130.4, 129.5, 126.6, 107.4, 62.1, 48.3, 27.9, 22.9.

後処理

  1. customto give the pH˜1
  2. extractionthe resulting mixture was extracted with DCM
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. customevaporated
  6. customthe crude residue was purified by preparative HPLC

出典と根拠

ORDレコード
ord-4001eec1932f4ee18f665a589582a9a9
出典データセット
uspto-grants-2011_06
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07960380B2

反応ノート

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