Acetic Acid → HCID 23541118, compound

HRID 1793259Notes

Reaction equation

HRID 1793259 reaction equation
C1(C[NH:8][CH:9]([C@:18]2([CH2:32][OH:33])[O:22][C@@H:21]([N:23]3[CH:30]=[CH:29][C:27](=[O:28])[NH:26][C:24]3=[O:25])[CH2:20][C@@H:19]2[OH:31])NCC2C=CC=CC=2)C=CC=CC=1.C1CCCCC=1.C(O)(=O)C.NC[C@]1(CO)O[C@@H](N2C=C(C)C(=O)NC2=O)C[C@@H]1O>[Pd].C(O)C>[NH2:8][CH2:9][C@:18]1([CH2:32][OH:33])[O:22][C@@H:21]([N:23]2[CH:30]=[CH:29][C:27](=[O:28])[NH:26][C:24]2=[O:25])[CH2:20][C@@H:19]1[OH:31]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 8079CyclohexeneHCID 22881721HCID 22881721, compoundHCID 86589979HCID 86589979, compound

Product 1

HCID 23541118HCID 23541118, compoundYield 101.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

4′-C-(1,1′-diphenylmethylaminomethyl)-2′-deoxyuridine (12) (0.056 g, 0.13 mmol) was treated with cyclohexene (1 mL), glacial acetic acid 0.5 mL) and 5% palladium on charcoal (0.06 g) in ethanol (5 mL) according to the procedure used for the preparation of compound (4). The crude product was purified by dissolving in water and washing with toluene. The aqueous layer was separated and the solvent removed under vacuum to give the title compound (13) as an amorphous solid (0.034 g, 100%). δH(300 MHz, D2O) 7.64(1H, d, H-6), 6.22(1H, dd, H-1′), 5.72(1H, d, H-5), 4.43(1H, m, H-3′), 3.56(2H, 2d, H-5′), 3.26(1H, d, CH2NH2), 3.05(1H, d, CH2NH2), 2.40(2H, m, H-2′); δC(75.45 MHz, D2O) 166.95, 152.46, 142.67, 103.11, 86.77, 86.43, 73.97, 64.82, 41.59, 39.25; ES +ve m/z 258(M+H)+, 242(M−NH3)+.

Workup

  1. customThe crude product was purified
  2. dissolutionby dissolving in water
  3. washwashing with toluene
  4. customThe aqueous layer was separated
  5. customthe solvent removed under vacuum

Sources & evidence

ORD record
ord-5d943e80966940b7bc9cb935cb92d36f
Source dataset
uspto-grants-2006_07
Patent number
US07078499B2

Reaction notes

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