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

HRID 491867ノート

反応式

HRID 491867 の反応式
[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]

参加物

7

反応物 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

生成物 1

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

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-4a6ecf75d0b94cc69bc799803035ae23
出典データセット
uspto-grants-2009_05
特許番号
US07531545B2

反応ノート

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