Hydrochloric Acid → [2-Cyano-5-(4,4-dimethyl-2-oxo-1,4-dihydro-2H-3,1-benzoxazin-6-yl)-1H-pyrrol-1-yl]acetic acid

HRID 412399ノート

反応式

HRID 412399 の反応式
C([O:5][C:6](=[O:28])[CH2:7][N:8]1[C:12]([C:13]2[CH:14]=[CH:15][C:16]3[NH:21][C:20](=[O:22])[O:19][C:18]([CH3:24])([CH3:23])[C:17]=3[CH:25]=2)=[CH:11][CH:10]=[C:9]1[C:26]#[N:27])(C)(C)C.[OH-].[Na+].Cl>C(O)C>[C:26]([C:9]1[N:8]([CH2:7][C:6]([OH:28])=[O:5])[C:12]([C:13]2[CH:14]=[CH:15][C:16]3[NH:21][C:20](=[O:22])[O:19][C:18]([CH3:24])([CH3:23])[C:17]=3[CH:25]=2)=[CH:11][CH:10]=1)#[N:27]

参加物

5

反応物 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 12044964tert-butyl[2-cyano-5-(4,4-dimethyl-2-oxo-1,4-dihydro-2H-3,1-benzoxazin-6-yl)-1H-pyrrol-1-yl]acetate

生成物 1

HCID 12044965[2-Cyano-5-(4,4-dimethyl-2-oxo-1,4-dihydro-2H-3,1-benzoxazin-6-yl)-1H-pyrrol-1-yl]acetic acid

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

A solution of tert-butyl[2-cyano-5-(4,4-dimethyl-2-oxo-1,4-dihydro-2H-3,1-benzoxazin-6-yl)-1H-pyrrol-1-yl]acetate (2.2 g, 5.8 mmol), and sodium hydroxide (1.6 g, 40 mmol) in ethanol (200 ml) was heated to reflux for 2 hours. After cooling to room temperature the mixture was acidified with diluted hydrochloric acid, and extracted with ethylacetate. The ethylacetate solution was dried over magnesium sulfate, filtered, and concentrated in vacuo. Recrystallization from ethylacetate/hexane afforded the title compound, m.p. 207-209° C. (1.2 g, 64%); 1H-NMR (DMSO-d6) δ 1.61 (s, 6H), 4.77 (s, 2H), 6.35 (d, J=4 Hz, 1H), 6.98 (d, J=8.1 Hz, 1H), 7.09 (d, j=4.1 Hz, 1H), 7.26 (m, 2H), 10.43 (s, 1H), MS (APCI (−)) m/z 324 (M−H)−.

後処理

  1. temperatureto reflux for 2 hours
  2. extractionextracted with ethylacetate
  3. dry with materialThe ethylacetate solution was dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customRecrystallization from ethylacetate/hexane

出典と根拠

ORDレコード
ord-fc3b920c49284984aa49e06a6e08cb01
出典データセット
uspto-grants-2003_05
特許番号
US06562857B2

反応ノート

読み込み中…