5-(6-Amino-2,4-dioxo-1,3-dipropyl-1,2,3,4-tetrahydro-pyrimidin-5-ylcarbamoyl)-bicyclo[3.2.1]octane-1-carboxylic acid ethyl ester → 5-(2,6-Dioxo-1,3-dipropyl-2,3,6,7-tetrahydro-1H-purin-8-yl)-bicyclo[3.2.1]octane-1-carboxylic acid

HRID 480104노트

반응식

HRID 480104 반응식
C([O:3][C:4]([C:6]12[CH2:13][C:10]([C:14](=O)[NH:15][C:16]3[C:17](=[O:30])[N:18]([CH2:27][CH2:28][CH3:29])[C:19](=[O:26])[N:20]([CH2:23][CH2:24][CH3:25])[C:21]=3[NH2:22])([CH2:11][CH2:12]1)[CH2:9][CH2:8][CH2:7]2)=[O:5])C>[OH-].[Na+].CO>[O:26]=[C:19]1[N:20]([CH2:23][CH2:24][CH3:25])[C:21]2[N:22]=[C:14]([C:10]34[CH2:13][C:6]([C:4]([OH:3])=[O:5])([CH2:12][CH2:11]3)[CH2:7][CH2:8][CH2:9]4)[NH:15][C:16]=2[C:17](=[O:30])[N:18]1[CH2:27][CH2:28][CH3:29]

참가 물질

4

반응물 1

HCID 670783425-(6-Amino-2,4-dioxo-1,3-dipropyl-1,2,3,4-tetrahydro-pyrimidin-5-ylcarbamoyl)-bicyclo[3.2.1]octane-1-carboxylic acid ethyl ester

생성물 1

HCID 98432695-(2,6-Dioxo-1,3-dipropyl-2,3,6,7-tetrahydro-1H-purin-8-yl)-bicyclo[3.2.1]octane-1-carboxylic acid수율 42.2%

시약·촉매·용매 2

HCID 887Methanol용매HCID 14798Sodium Hydroxide용매

실험 절차

A solution of 5-(6-amino-2,4-dioxo-1,3-dipropyl-1,2,3,4-tetrahydro-pyrimidin-5-ylcarbamoyl)-bicyclo[3.2.1]octane-1-carboxylic acid ethyl ester (0.238 mmol, 0.10 g) in 20% NaOH (2.0 ml) and MeOH (10.0 ml) was stirred and refluxed 5 h. The reaction was cooled to room temperature and then concentrated to remove MeOH. The aqueous was acidified (pH 2-3) with conc. HCl and then extracted with EtOAc. The combined EtOAc extracts were washed with H2O and brine, and dried (MgSO4). Filtration and evaporation followed by reverse phase HPLC provided product (0.039 g, 42%) as a solid. MS (ES+) 389.12 (M+H, 100%)

후처리

  1. temperaturerefluxed 5 h
  2. concentrationconcentrated
  3. customto remove MeOH
  4. extractionextracted with EtOAc
  5. washThe combined EtOAc extracts were washed with H2O and brine
  6. dry with materialdried (MgSO4)
  7. filtrationFiltration and evaporation

출처 및 근거

ORD 기록
ord-4a6151ecd1124a5092bd070c15cf162c
출처 데이터셋
uspto-grants-2003_11
특허 번호
US06649600B1

반응 노트

불러오는 중…