Formaldehyde → HCID 57270233, compound

HRID 1384713Notes

Reaction equation

HRID 1384713 reaction equation
C(O[C:9]([N:11]1C=CC=[C:13]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[N:12]1[C:24](=[O:49])[CH:25]([N:38]1[C:42](=[O:43])[C:41]2=[CH:44][CH:45]=[CH:46][CH:47]=[C:40]2[C:39]1=[O:48])[CH2:26]NC(OCC1C=CC=CC=1)=O)=O)C1C=CC=CC=1.C=O>CO.[Pd]>[O:49]=[C:24]1[N:12]2[C@@H:13]([C:17]([O:19][C:20]([CH3:22])([CH3:23])[CH3:21])=[O:18])[NH:12][CH2:24][CH2:25][CH2:26][N:11]2[CH2:9][CH2:26][C@@H:25]1[N:38]1[C:42](=[O:43])[C:41]2=[CH:44][CH:45]=[CH:46][CH:47]=[C:40]2[C:39]1=[O:48]

Participants

5

Reactant 2

HCID 712FormaldehydeHCID 19592033HCID 19592033, compound

Product 1

HCID 57270233HCID 57270233, compoundYield 94.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of ester 267 (50 mg, 0.074 mmol) in methanol (15 ml) was treated with 10% palladium on carbon (50 mg) and hydrogenated at room temperature and atmospheric pressure for 24 h. The mixture was evacuated thoroughly to remove hydrogen then treated with 37% aqueous formaldehyde (18 mg, 0.22 mmol) and stirred under nitrogen for 2 h. The mixture was filtered, evaporated to dryness and the product purified by flash chromatography (4-100% ethyl acetate/dichloromethane) to afford 268 14.5 mg (48%) as an oil: 1H NMR (CDCl3) δ 7.85 (2H, m), 7.71 (2H, m), 5.78 (1H, dd, J=10, 5), 4.99 (1H, dd, J=6.1, 1.5), 4.07 (1H, d, J=10.6), 3.49 (1H, dd, J=14, 5), 3.39 (1H, d, J=10.3), 3.24 (1H, dd, J=14, 10.2), 3.17 (2H, m), 2.39 (1H, m), 1.84-1.46 (3H), 1.51 (9H, s); MS (ES+), 415 (M+1), 437 (M+Na)

Workup

  1. customThe mixture was evacuated thoroughly
  2. customto remove hydrogen
  3. filtrationThe mixture was filtered
  4. customevaporated to dryness
  5. customthe product purified by flash chromatography (4-100% ethyl acetate/dichloromethane)

Sources & evidence

ORD record
ord-ea14a414d7e64fddbc77a7025de389c0
Source dataset
uspto-grants-2001_07
Patent number
US06258948B1

Reaction notes

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