Isopropyl chloroformate → (3S,4S)-3-[2-(4-Methoxy-benzyl)-1-oxo-2,8-diaza-spiro[4.5]dec-8-ylmethyl]-4-phenyl-pyrrolidine-1-carboxylic Acid Isopropyl Ester Hydrochloride

HRID 1182172노트

반응식

HRID 1182172 반응식
[CH3:1][O:2][C:3]1[CH:32]=[CH:31][C:6]([CH2:7][N:8]2[CH2:12][CH2:11][C:10]3([CH2:17][CH2:16][N:15]([CH2:18][C@@H:19]4[C@@H:23]([C:24]5[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=5)[CH2:22][NH:21][CH2:20]4)[CH2:14][CH2:13]3)[C:9]2=[O:30])=[CH:5][CH:4]=1.[CH:33]([O:36][C:37]([Cl:39])=[O:38])([CH3:35])[CH3:34].C(N(CC)CC)C.C(=O)(O)[O-].[Na+]>C(Cl)Cl>[ClH:39].[CH:33]([O:36][C:37]([N:21]1[CH2:22][C@H:23]([C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=2)[C@@H:19]([CH2:18][N:15]2[CH2:16][CH2:17][C:10]3([C:9](=[O:30])[N:8]([CH2:7][C:6]4[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:32][CH:31]=4)[CH2:12][CH2:11]3)[CH2:13][CH2:14]2)[CH2:20]1)=[O:38])([CH3:35])[CH3:34]

참가 물질

6

반응물 4

HCID 7917Isopropyl chloroformateHCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 114646642-(4-Methoxy-benzyl)-8-((3R,4S)-4-phenyl-pyrrolidin-3-ylmethyl)-2,8-diaza-spiro[4.5]decan-1-one

생성물 1

HCID 67368814(3S,4S)-3-[2-(4-Methoxy-benzyl)-1-oxo-2,8-diaza-spiro[4.5]dec-8-ylmethyl]-4-phenyl-pyrrolidine-1-carboxylic Acid Isopropyl Ester Hydrochloride수율 50%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a solution of 2-(4-methoxy-benzyl)-8-((3R,4S)-4-phenyl-pyrrolidin-3-ylmethyl)-2,8-diaza-spiro[4.5]decan-1-one (60 μmol) in anhydrous DCM (1 mL) was added isopropylchloroformate (180 μL, 1M in toluene, 180 μmol) and triethylamine (29 μL, 55 μmol). The reaction mixture was stirred overnight at room temperature. Saturated sodium bicarbonate aqueous solution was added to the reaction mixture and the aqueous layer washed with dichloromethane (3×2 mL). The organic layer was then concentrated in vacuo and purified by semi-preparative HPLC (Method D) and lyophilized to give the Compound 183 as a colorless solid (15.3 mg, 50%).

후처리

  1. washthe aqueous layer washed with dichloromethane (3×2 mL)
  2. concentrationThe organic layer was then concentrated in vacuo
  3. custompurified by semi-preparative HPLC (Method D)

출처 및 근거

ORD 기록
ord-b70cd91e2a464b3f99dfe0e0782d4201
출처 데이터셋
uspto-grants-2007_10
특허 번호
US07288548B2

반응 노트

불러오는 중…