Pyridine → HCID 136367326, 화합물

HRID 227252노트

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HRID 227252 반응식
[C:1]([O:5][C:6]([N:8]1[CH:12]([C:13]2[C:17]3[N:18]=[CH:19][NH:20][C:21](=[O:22])[C:16]=3[NH:15][CH:14]=2)[CH:11]([OH:23])[CH:10]([OH:24])[CH:9]1[CH2:25][OH:26])=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:27](Cl)(=[O:34])[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.[C:36]([O-:39])(O)=O.[Na+].C([O:44][CH2:45][CH3:46])(=O)C.N1[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=1>CN(C1C=CN=CC=1)C>[C:1]([O:5][C:6]([N:8]1[CH:12]([C:13]2[C:17]3[N:18]=[CH:19][NH:20][C:21](=[O:22])[C:16]=3[NH:15][CH:14]=2)[CH:11]([O:23][C:27](=[O:34])[C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH:10]([O:24][C:45](=[O:44])[C:46]2[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=2)[CH:9]1[CH2:25][O:26][C:36](=[O:39])[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

참가 물질

7

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HCID 1049PyridineHCID 7412Benzoyl chlorideHCID 8857Ethyl AcetateHCID 516892Sodium BicarbonateHCID 136367327HCID 136367327, 화합물

생성물 1

HCID 136367326HCID 136367326, 화합물수율 58.5%

시약·촉매·용매 1

HCID 142844-(Dimethylamino)pyridine촉매

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온도
55 °C

실험 절차

To a stirred solution of compound 1-2 from step 1 (5.85 g, 16.0 mmol) in pyridine (80 mL) is added benzoyl chloride (13.49 g, 96 mmol) and DMAP (0.05 g, 0.4 mmol) at RT. The reaction mixture is heated to 55° C. and then cooled to RT and stirred for 72 h. The reaction mixture is poured into saturated NaHCO3 (400 mL) and ethyl acetate (250 mL) and stirred for 1.5 h. The reaction mixture is extracted with ethyl acetate (2×1 L) and the combined organic extracts are washed with cold HCl (0.1 N, 400 mL), saturated NaHCO3 (1×200 mL), water (2×200 mL), and brine (1×250 mL) and dried (MgSO4). After filtration, the filtrate is concentrated and the crude residue is purified on silica gel column by flash chromatography using ethyl acetate in hexanes (0 to 100%) to afford 6.35 g (58.5%) of 3,4-bis-benzoyloxy-2-benzoyloxymethyl-5-(4-oxo-4,5-dihydro-3H-pyrrolo[3,2-d]pyrimidin-7-yl)-pyrrolidine-1-carboxylic acid tert-butyl ester (1-3) as a gum.

후처리

  1. temperaturecooled to RT
  2. stirringstirred for 1.5 h
  3. extractionThe reaction mixture is extracted with ethyl acetate (2×1 L)
  4. washthe combined organic extracts are washed with cold HCl (0.1 N, 400 mL), saturated NaHCO3 (1×200 mL), water (2×200 mL), and brine (1×250 mL)
  5. dry with materialdried (MgSO4)
  6. filtrationAfter filtration
  7. concentrationthe filtrate is concentrated
  8. customthe crude residue is purified on silica gel column by flash chromatography

출처 및 근거

ORD 기록
ord-82c0df05b03945f897b598094ffa1bb0
출처 데이터셋
uspto-grants-2009_07
특허 번호
US07560434B2

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