Hydrochloric Acid → 3-phenyl-6-(3-phenylpropyloxy)-1-oxo-1H-indene-2-carboxylate cyclohexylamide

HRID 17897

反応式

HRID 17897 の反応式
[C:1]1([C:7]2[C:15]3[C:10](=[CH:11][C:12]([O:16][CH2:17][CH2:18][CH2:19][C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=4)=[CH:13][CH:14]=3)[C:9](=[O:26])[C:8]=2[C:27]([O-:29])=[O:28])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(N(CC)CC)C.[CH:37]1([NH2:43])[CH2:42][CH2:41][CH2:40][CH2:39][CH2:38]1.O=C1N(P(Cl)(N2CCOC2=O)=O)CCO1.Cl>ClCCl.O>[CH:37]1([NH-:43])[CH2:42][CH2:41][CH2:40][CH2:39][CH2:38]1.[C:1]1([C:7]2[C:15]3[C:10](=[CH:11][C:12]([O:16][CH2:17][CH2:18][CH2:19][C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=4)=[CH:13][CH:14]=3)[C:9](=[O:26])[C:8]=2[C:27]([O-:29])=[O:28])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

参加物

8

反応物 5

HCID 313Hydrochloric AcidHCID 7965CyclohexylamineHCID 8471TriethylamineHCID 152842Bis(2-oxo-3-oxazolidinyl)phosphinic chlorideHCID 866140333-Phenyl-6-(3-phenylpropyloxy)-1-oxo-1H-indene-2-carboxylate

生成物 1

HCID 866140323-phenyl-6-(3-phenylpropyloxy)-1-oxo-1H-indene-2-carboxylate cyclohexylamide収率 59.8%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6344Dichloromethane溶媒

実験手順

3-Phenyl-6-(3-phenylpropyloxy)-1-oxo-1H-indene-2-carboxylate (200 mg, 0.52 mmol) was dissolved in dichloromethane (10 ml). Triethylamine (240 μl, 1.72 mmol) and cyclohexylamine (59 μl, 0.52 mmol) were added thereto at 10° C. Then, after adding bis(2-oxo-3-oxazolidinyl)phosphinic chloride (137 mg, 0.52 mmol), the reaction mixture was stirred for about 20 min at room temperature followed by additional 1 hour at 10° C. After the water was added thereto to complete the reaction, pH was adjusted to 1˜1.5 with 4N hydrochloric acid. The mixture was washed with brine, and extracted with dichloromethane. The extract was dried over anhydrous sulfonate sulfate, concentrated, and the resulting residue was purified by column chromatography (ethyl acetate:hexane=1:9˜2:8) to obtain the title compound (yield 59.8%) as a red solid.

後処理

  1. customat 10° C
  2. waitfollowed by additional 1 hour at 10° C
  3. customthe reaction, pH
  4. washThe mixture was washed with brine
  5. extractionextracted with dichloromethane
  6. dry with materialThe extract was dried over anhydrous sulfonate sulfate
  7. concentrationconcentrated
  8. customthe resulting residue was purified by column chromatography (ethyl acetate:hexane=1:9˜2:8)

出典と根拠

ORDレコード
ord-b7a74c8b2c8249d2bb1e621f9135b741
出典データセット
uspto-grants-2010_06
特許番号
US07741323B2

関連ノート

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