Triethylamine → ((R)-1-dimethylcarbamoyl-3-methyl-butyl)-carbamic acid tert-butyl ester

HRID 446947노트

반응식

HRID 446947 반응식
O.[C:2]([NH:9][C@@H:10]([C:15]([OH:17])=O)[CH2:11][CH:12]([CH3:14])[CH3:13])([O:4][C:5]([CH3:8])([CH3:7])[CH3:6])=[O:3].[CH2:18]([N:20](CC)[CH2:21]C)C.Cl.CNC.C1CN([P+](ON2N=NC3C=CC=CC2=3)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F>CN(C=O)C.CCOC(C)=O>[C:5]([O:4][C:2](=[O:3])[NH:9][C@@H:10]([C:15](=[O:17])[N:20]([CH3:21])[CH3:18])[CH2:11][CH:12]([CH3:14])[CH3:13])([CH3:8])([CH3:7])[CH3:6]

참가 물질

7

반응물 4

HCID 8471TriethylamineHCID 10473Dimethylamine, hydrochlorideHCID 2724699PyBOPHCID 2724763D-Leucine, N-[(1,1-dimethylethoxy)carbonyl]-, monohydrate

생성물 1

HCID 28165661((R)-1-dimethylcarbamoyl-3-methyl-butyl)-carbamic acid tert-butyl ester수율 58%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

To a solution of Boc-D-leucine monohydrate (2.0 g, 8.0 mmol), triethylamine (5.6 mL, 40.1 mmol), and dimethylamine hydrochloride (1.31 g, 16.0 mmol) in DMF (15 mL) at room temperature was added PyBOP (4.59 g, 8.82 mmol). The reaction mixture was stirred overnight then diluted with EtOAc (50 mL) and washed with water (4×50 mL). The combined organic extracts were dried (Na2SO4) and evaporated under vacuum. The crude residue was purified by SiO2 chromatography (80 g, hexanes/EtOAc, 1:1) to give 1.19 g (58%) of ((R)-1-dimethylcarbamoyl-3-methyl-butyl)-carbamic acid tert-butyl ester as a colorless viscous oil.

후처리

  1. washwashed with water (4×50 mL)
  2. dry with materialThe combined organic extracts were dried (Na2SO4)
  3. customevaporated under vacuum
  4. customThe crude residue was purified by SiO2 chromatography (80 g, hexanes/EtOAc, 1:1)

출처 및 근거

ORD 기록
ord-948d16f949124e3abb92073d9e0fda0f
출처 데이터셋
uspto-grants-2013_07
특허 번호
US08481541B2

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