Hydrochloric Acid → HCID 178453598、化合物

HRID 1984891ノート

反応式

HRID 1984891 の反応式
[C:1]([O:5][C:6](=[O:24])[NH:7][CH2:8][C@H:9]1[CH2:14][CH2:13][C@@H:12]([CH2:15][NH:16]C(OC(C)(C)C)=O)[CH2:11][CH2:10]1)([CH3:4])([CH3:3])[CH3:2].Cl.CC(OC(OC(OC(C)(C)C)=O)=O)(C)C>C(Cl)Cl.CCOC(C)=O>[C:1]([O:5][C:6](=[O:24])[NH:7][CH2:8][C@H:9]1[CH2:10][CH2:11][C@@H:12]([CH2:15][NH2:16])[CH2:13][CH2:14]1)([CH3:4])([CH3:2])[CH3:3]

参加物

6

反応物 3

HCID 313Hydrochloric AcidHCID 90495Di-tert-butyl dicarbonateHCID 178453602HCID 178453602、化合物

生成物 1

HCID 178453598HCID 178453598、化合物収率 14.1%

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒HCID 8857Ethyl Acetate溶媒

実験手順

To a solution of cis-[4-(tert-butoxycarbonylamino-methyl)-cyclohexylmethyl]-carbamic acid tert-butyl ester (2.55 g, 7.45 mmol) in CH2Cl2 (40 mL) was added 4 M hydrogen chloride in EtOAc (4 mL). The reaction mixture was stirred at ambient temperature for 5 hr and concentrated. The residue was dissolved in 1,4-dioxane (20 mL) and 10% aqueous sodium hydroxide (40 mL) and the resulting solution was cooled on an ice-bath. (Boc)2O (829 mg, 3.80 mmol) was added dropwise and the mixture was stirred at ambient temperature for 3 h. The aqueous layer was extracted with CHCl3 (three times). The combined organic layer was dried over MgSO4, filtered and concentrated, and purified by flash chromatography (silica gel, 9% MeOH in CHCl3) to give cis-(4-aminomethyl-cyclohexylmethyl)-carbamic acid tert-butyl ester (255 mg, 14%) as a pale yellow oil.

後処理

  1. concentrationconcentrated
  2. dissolutionThe residue was dissolved in 1,4-dioxane (20 mL)
  3. temperature10% aqueous sodium hydroxide (40 mL) and the resulting solution was cooled on an ice-bath
  4. stirringthe mixture was stirred at ambient temperature for 3 h
  5. extractionThe aqueous layer was extracted with CHCl3 (three times)
  6. dry with materialThe combined organic layer was dried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. custompurified by flash chromatography (silica gel, 9% MeOH in CHCl3)

出典と根拠

ORDレコード
ord-3b9f2904d7cf4d33abc97f695a26e428
出典データセット
uspto-grants-2009_06
特許番号
US07544690B2

反応ノート

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