Hydrochloric Acid → (R)-2-tert-butoxycarbonylamino-4-(4-heptyloxy-phenyl)-2-methyl-butyric acid

HRID 12586

反応式

HRID 12586 の反応式
[C:1]([O:5][C:6](=[O:28])[NH:7][C@:8]([CH:26]=[O:27])([CH3:25])[CH2:9][CH2:10][C:11]1[CH:16]=[CH:15][C:14]([O:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])=[CH:13][CH:12]=1)([CH3:4])([CH3:3])[CH3:2].CC(=CC)C.Cl([O-])=[O:35].[Na+].Cl>C(O)(C)(C)C.OP([O-])(O)=O.[K+].CCOC(C)=O>[C:1]([O:5][C:6]([NH:7][C@:8]([CH3:25])([CH2:9][CH2:10][C:11]1[CH:16]=[CH:15][C:14]([O:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])=[CH:13][CH:12]=1)[C:26]([OH:35])=[O:27])=[O:28])([CH3:2])([CH3:4])[CH3:3]

参加物

8

反応物 4

HCID 313Hydrochloric AcidHCID 105532-Methyl-2-buteneHCID 23668197Sodium ChloriteHCID 59339517[(R)-1-Formyl-3-(4-heptyloxy-phenyl)-1-methyl-propyl]-carbamic acid tert-butyl ester

生成物 1

HCID 58897679(R)-2-tert-butoxycarbonylamino-4-(4-heptyloxy-phenyl)-2-methyl-butyric acid

試薬・触媒・溶媒 3

HCID 6386tert-Butanol溶媒HCID 8857Ethyl Acetate溶媒HCID 516951Monobasic potassium phosphate溶媒

実験手順

To a stirred solution of [(R)-1-formyl-3-(4-heptyloxy-phenyl)-1-methyl-propyl]-carbamic acid tert-butyl ester (103 mg, 0.26 mMol) in tert-butanol (1 ml) and 10% aqueous KH2PO4 (1 ml) is added 2-methyl-2-butene (0.66 ml, 5.27 mMol) and sodium chlorite (59 mg, 0.52 mMol). The mixture is stirred at RT for 1 hour. The reaction mixture is then poured onto a biphasic mixture of AcOEt and HCl (aqueous, 1M). The aqueous phase is extracted twice with AcOEt. The combined organic layers are washed with a small amount of NaHCO3 (saturated aqueous solution), dried (Na2SO4) and concentrated under reduced pressure. Column chromatography eluting with 5% MeOH in CH2Cl2 gives the title compound as a colourless oil.

後処理

  1. extractionThe aqueous phase is extracted twice with AcOEt
  2. washThe combined organic layers are washed with a small amount of NaHCO3 (saturated aqueous solution)
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated under reduced pressure
  5. washColumn chromatography eluting with 5% MeOH in CH2Cl2

出典と根拠

ORDレコード
ord-ed19de40aa354320974dd94b4cf5e358
出典データセット
uspto-grants-2010_06
特許番号
US07728020B2

関連ノート

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