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Methanol → 4-[8-(3-Methylsulfanyl-phenyl)-[1,7]naphthyridin-6-yl]-cyclohexanecarboxylic acid

HRID 917320
ノート
印刷プレビュー

反応式

HRID 917320 の反応式
[OH-].[Li+].C([O:5][C:6]([CH:8]1[CH2:13][CH2:12][CH:11]([C:14]2[CH:15]=[C:16]3[C:21](=[C:22]([C:24]4[CH:29]=[CH:28][CH:27]=[C:26]([S:30][CH3:31])[CH:25]=4)[N:23]=2)[N:20]=[CH:19][CH:18]=[CH:17]3)[CH2:10][CH2:9]1)=[O:7])C.CO>O.C1COCC1>[CH3:31][S:30][C:26]1[CH:25]=[C:24]([C:22]2[N:23]=[C:14]([CH:11]3[CH2:10][CH2:9][CH:8]([C:6]([OH:7])=[O:5])[CH2:13][CH2:12]3)[CH:15]=[C:16]3[C:21]=2[N:20]=[CH:19][CH:18]=[CH:17]3)[CH:29]=[CH:28][CH:27]=1
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 3

HCID 887MethanolHCID 3939Lithium HydroxideHCID 11361771HCID 11361771、化合物

生成物 1

HCID 101996814-[8-(3-Methylsulfanyl-phenyl)-[1,7]naphthyridin-6-yl]-cyclohexanecarboxylic acid

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

Lithium hydroxide (168 mg, 1.76 mmol) in water (1.7 ml) is added to a solution of 4-[8-(3-methylsulfanyl-phenyl)-[1,7]naphthyridin-6-yl]-cyclohexanecarboxylic acid ethyl ester (650 mg, 1.6 mmol) in THF (3.2 ml) under argon. Methanol is added to maintain solution (4 ml) and the mixture is stirred at room temperature for 5 hours. The mixture is evaporated to dryness then partitioned between ethyl acetate and water. The aqueous layer is acidified to pH 2 then extracted into ethylacetate and dried over magnesium sulfate, Evaporation gives a green gum which is reevaporated from methanol then DCM/diethylether to give a yellow/green foam. The foam is triturated with 3:1 hexane:diethyl ether, 2:1 hexane:diethylether, ethylacetate/hexane/ether mixtures and finally 5:1 diethylether:ethanol to yield an off-white solid. This is then recrystallised from ethanol to yield the title compound. M.p 177.6-178.2° C., MS (AP+) 379.05

後処理

  1. customThe mixture is evaporated to dryness
  2. customthen partitioned between ethyl acetate and water
  3. extractionthen extracted into ethylacetate
  4. dry with materialdried over magnesium sulfate, Evaporation
  5. customgives a green gum which
  6. customis reevaporated from methanol
  7. customDCM/diethylether to give a yellow/green foam
  8. customThe foam is triturated with 3:1 hexane
  9. customdiethyl ether, 2:1 hexane:diethylether, ethylacetate/hexane/ether mixtures and finally 5:1 diethylether:ethanol to yield an off-white solid
  10. customThis is then recrystallised from ethanol

出典と根拠

ORDレコード
ord-f7a91bdeab4944c6a8ccefc7cddd2586
出典データセット
uspto-grants-2007_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07273875B2

反応ノート

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