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Ethyl Acetate → HCID 68583507、化合物

HRID 12582
ノート
印刷プレビュー

反応式

HRID 12582 の反応式
[C:1]([O:5][C:6]([N:8]1[C@@:12]([CH2:14][CH2:15][C:16]2[CH:21]=[CH:20][C:19]([O:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29])=[CH:18][CH:17]=2)([CH3:13])[CH2:11]OS1(=O)=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].[C-:32]#[N:33].[Na+].CCOC(C)=O.C([O-])(O)=O.[Na+]>CN(C=O)C>[C:1]([O:5][C:6](=[O:7])[NH:8][C@:12]([CH2:11][C:32]#[N:33])([CH3:13])[CH2:14][CH2:15][C:16]1[CH:17]=[CH:18][C:19]([O:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29])=[CH:20][CH:21]=1)([CH3:4])([CH3:3])[CH3:2]
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 4

HCID 8857Ethyl AcetateHCID 8929Sodium Cyanide2 回HCID 516892Sodium BicarbonateHCID 58897685(R)-4-[2-(4-heptyloxy-phenyl)-ethyl]-4-methyl-2,2-dioxo-2lambda*6*-[1,2,3]oxathiazolidine-3-carboxylic acid tert-butyl ester

生成物 1

HCID 68583507HCID 68583507、化合物

試薬・触媒・溶媒 1

HCID 6228
Dimethylformamide
溶媒

実験手順

To a stirred solution of (R)-4-[2-(4-heptyloxy-phenyl)-ethyl]-4-methyl-2,2-dioxo-2λ*6*-[1,2,3]oxathiazolidine-3-carboxylic acid tert-butyl ester (174 mg, 0.40 mMol) in DMF (5 ml) is added sodium cyanide (94 mg, 1.91 mMol). The mixture is stirred at RT for 25 hours. Additional sodium cyanide (37 mg, 0.76 mMol) is added and the mixture is stirred at RT for 18 hours. The reaction mixture is then poured onto a biphasic mixture of AcOEt and NaHCO3 (saturated aqueous solution). The aqueous phase is extracted twice with AcOEt. The combined organic layers are dried (Na2SO4) and concentrated under reduced pressure. Column chromatography eluting with 5% AcOEt in toluene gives the title compound as a colourless oil.

後処理

  1. stirringthe mixture is stirred at RT for 18 hours
  2. extractionThe aqueous phase is extracted twice with AcOEt
  3. dry with materialThe combined organic layers are dried (Na2SO4)
  4. concentrationconcentrated under reduced pressure
  5. washColumn chromatography eluting with 5% AcOEt in toluene

出典と根拠

ORDレコード
ord-ddefdcac9e5747c6b7cfd8a0a67b1f46
出典データセット
uspto-grants-2010_06
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07728020B2

反応ノート

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