1-Hydroxybenzotriazole → [Cyclohexyl-(methoxy-methyl-carbamoyl)-methyl]-carbamic acid tert-butyl ester

HRID 491867노트

반응식

HRID 491867 반응식
[CH3:1][C:2]([O:5][C:6]([NH:8][C@@H:9]([C:16]([OH:18])=O)[CH:10]1[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]1)=[O:7])([CH3:4])[CH3:3].Cl.[CH3:20][NH:21][O:22][CH3:23].C1C=CC2N(O)N=NC=2C=1.CNC(N=C=NCC)CCNC>C(Cl)Cl.CCOC(C)=O>[C:2]([O:5][C:6](=[O:7])[NH:8][CH:9]([CH:10]1[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15]1)[C:16](=[O:18])[N:21]([O:22][CH3:23])[CH3:20])([CH3:1])([CH3:3])[CH3:4]

참가 물질

7

반응물 4

HCID 757711-HydroxybenzotriazoleHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 7014890(2R)-2-(((tert-butoxy)carbonyl)amino)-2-cyclohexylacetic acidHCID 230638731,3-Dimethylaminopropyl-3-ethylcarbodiimide

생성물 1

HCID 72442761[Cyclohexyl-(methoxy-methyl-carbamoyl)-methyl]-carbamic acid tert-butyl ester

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 8857Ethyl Acetate용매

실험 절차

To an ice cooled solution of Boc-D-cyclohexylglycine (10 g, 39 mmol) in DCM (200 mL), N,O-dimethylhydroxyamine HCl salt (4.6 g, 46 mmol), HOBT (7 g, 51 mmol), and TEA (11 mL) were added followed by addition of 1,3-dimethylamino propyl-3-ethylcarbodiimide (EDC, 10 g, 51 mmol). The reaction mixture was allowed to warm to room temperature and then stirred overnight. EtOAc (300 mL) was added. The resulting solution washed with aqueous citric acid solution, aqueous NaHCO3 solution, and aqueous NaCl solution. The organic layer was separated, dried with MgSO4, and then evaporated to yield [cyclohexyl-(methoxy-methyl-carbamoyl)-methyl]-carbamic acid tert-butyl ester as a colorless oil, which was used in the next step without further purification.

후처리

  1. washThe resulting solution washed with aqueous citric acid solution, aqueous NaHCO3 solution, and aqueous NaCl solution
  2. customThe organic layer was separated
  3. dry with materialdried with MgSO4
  4. customevaporated

출처 및 근거

ORD 기록
ord-4a6ecf75d0b94cc69bc799803035ae23
출처 데이터셋
uspto-grants-2009_05
특허 번호
US07531545B2

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