Ammonium cerium (IV) nitrate → Acetic acid 4-oxo-4,5,6,7-tetrahydro-pyrazolo[1,5-a]pyrazin-2-ylmethyl ester

HRID 2046214노트

반응식

HRID 2046214 반응식
[N+]([O-])([O-])=O.[Ce+4].[NH4+].[N+]([O-])([O-])=O.[N+]([O-])([O-])=O.[N+]([O-])([O-])=O.[N+]([O-])([O-])=O.COC1C=CC(C[N:30]2[CH2:35][CH2:34][N:33]3[N:36]=[C:37]([CH2:39][O:40][C:41](=[O:43])[CH3:42])[CH:38]=[C:32]3[C:31]2=[O:44])=CC=1>O.C(#N)C>[O:44]=[C:31]1[NH:30][CH2:35][CH2:34][N:33]2[N:36]=[C:37]([CH2:39][O:40][C:41](=[O:43])[CH3:42])[CH:38]=[C:32]12

참가 물질

5

반응물 2

HCID 9869224Ammonium cerium (IV) nitrateHCID 67975764Acetic acid 5-(4-methoxy-benzyl)-4-oxo-4,5,6,7-tetrahydro-pyrazolo[1,5-a]pyrazin-2-ylmethyl ester

생성물 1

HCID 67974158Acetic acid 4-oxo-4,5,6,7-tetrahydro-pyrazolo[1,5-a]pyrazin-2-ylmethyl ester수율 62.3%

시약·촉매·용매 2

HCID 962Water용매HCID 6342Acetonitrile용매

실험 절차

A solution of ammonium cerium (IV) nitrate (0.7 g, 1.29 mmol) in water (1.1 mL) was added to a stirred solution of acetic acid 5-(4-methoxy-benzyl)-4-oxo-4,5,6,7-tetrahydro-pyrazolo[1,5-a]pyrazin-2-ylmethyl ester (142 mg, 0.43 mmol) in ACN (4.3 mL). The mixture was stirred at room temperature for 30 minutes and the solvents evaporated in vacuo. The crude product was purified by flash column chromatography (silica, 7 N solution of ammonia in MeOH in DCM 0/100 to 10/90). The desired fractions were collected and concentrated in vacuo to yield acetic acid 4-oxo-4,5,6,7-tetrahydro-pyrazolo[1,5-a]pyrazin-2-ylmethyl ester (56 mg, 62% yield) as a white solid.

후처리

  1. customthe solvents evaporated in vacuo
  2. customThe crude product was purified by flash column chromatography (silica, 7 N solution of ammonia in MeOH in DCM 0/100 to 10/90)
  3. customThe desired fractions were collected
  4. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-0635435dcb23452e8f829673803a4dfc
출처 데이터셋
uspto-grants-2013_11
특허 번호
US08592422B2

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