Hydrochloric Acid → 3-Oxo-2-oxabicyclo[2.2.1]heptane-5-carboxylic acid

HRID 643835ノート

反応式

HRID 643835 の反応式
[OH-].[Na+].C[O:4][C:5]([C:7]1[CH:11]([C:12](=[O:26])N[C@]2(C(OC(C)(C)C)=O)C[C@H]2C=C)[CH2:10][CH:9]([O:27]C2C3C(=CC(OC)=CC=3)N=C(C3C=CC=CC=3)C=2)[CH:8]=1)=[O:6].Cl>CO>[O:26]=[C:12]1[CH:11]2[CH2:10][CH:9]([CH2:8][CH:7]2[C:5]([OH:4])=[O:6])[O:27]1

参加物

5

反応物 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 592041875-((1R,2S)-1-tert-Butoxycarbonyl-2-vinyl-cyclopropylcarbamoyl)-3-(7-methoxy-2-phenyl-quinolin-4-yloxy)-cyclopent-1-enecarboxylic acid methyl ester

生成物 1

HCID 462449653-Oxo-2-oxabicyclo[2.2.1]heptane-5-carboxylic acid収率 89.3%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

Sodium hydroxide (1M, 74 mL, 0.074 mol) was added to a stirred solution of 30 (3.73 g, 0.018 mol) in methanol (105 mL) at room temperature. After 4 h, the reaction mixture was neutralized with 3M HCl, evaporated and co-evaporated with toluene several times. Pyridine (75 mL) and Ac2O (53 mL) were added and the reaction mixture was allowed to shake overnight at room temperature. The mixture was then co-evaporated with toluene and purified by flash column chromatography (ethyl acetate+1% acetic acid) to give the title compound (2.51 g, 88%) as a yellow oil.

後処理

  1. customevaporated
  2. additionPyridine (75 mL) and Ac2O (53 mL) were added
  3. waitto shake overnight at room temperature
  4. custompurified by flash column chromatography (ethyl acetate+1% acetic acid)

出典と根拠

ORDレコード
ord-857a6a3b613749dab517a62fd97aa7e8
出典データセット
uspto-grants-2010_04
特許番号
US07700552B2

反応ノート

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