Pyridine → HCID 136367326, compound

HRID 227252Notes

Reaction equation

HRID 227252 reaction equation
[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]

Participants

7

Reactant 5

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

Product 1

HCID 136367326HCID 136367326, compoundYield 58.5%

Reagents, catalysts & solvents 1

HCID 142844-(Dimethylamino)pyridineCatalyst

Conditions

Temperature
55 °C

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-82c0df05b03945f897b598094ffa1bb0
Source dataset
uspto-grants-2009_07
Patent number
US07560434B2

Reaction notes

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