Hydrochloric Acid → HCID 178453598, 화합물

HRID 1984891노트

반응식

HRID 1984891 반응식
[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]

참가 물질

6

반응물 3

HCID 313Hydrochloric AcidHCID 90495Di-tert-butyl dicarbonateHCID 178453602HCID 178453602, 화합물

생성물 1

HCID 178453598HCID 178453598, 화합물수율 14.1%

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 8857Ethyl Acetate용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-3b9f2904d7cf4d33abc97f695a26e428
출처 데이터셋
uspto-grants-2009_06
특허 번호
US07544690B2

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