Sodium Formate → HCID 135540573, compound

HRID 989430Notes

Reaction equation

HRID 989430 reaction equation
C([O-])=O.[Na+].[CH3:5][O:6][C:7]1[CH:54]=[CH:53][C:10]([C:11]([O:26][CH2:27][C@@:28]23[C@@H:34]([O:35]CC4C=CC=CC=4)[C@@H:31]([O:32][CH2:33]2)[C@H:30]([N:43]2[CH:51]=[N:50][C:49]4[C:48](=[O:52])[NH:47][CH:46]=[N:45][C:44]2=4)[O:29]3)([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:12]2[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=2)=[CH:9][CH:8]=1>CO.ClCCl.[Pd]>[CH3:19][O:18][C:15]1[CH:16]=[CH:17][C:12]([C:11]([O:26][CH2:27][C@@:28]23[C@@H:34]([OH:35])[C@@H:31]([O:32][CH2:33]2)[C@H:30]([N:43]2[CH:51]=[N:50][C:49]4[C:48](=[O:52])[NH:47][CH:46]=[N:45][C:44]2=4)[O:29]3)([C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)[C:10]2[CH:53]=[CH:54][C:7]([O:6][CH3:5])=[CH:8][CH:9]=2)=[CH:13][CH:14]=1

Participants

6

Reactant 2

HCID 2723810Sodium FormateHCID 135481079HCID 135481079, compound

Product 1

HCID 135540573HCID 135540573, compoundYield 224.5%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

Sodium formate (1.2 g) was added to a mixture of compound 24 (1.02 g, 0.52 mmol) and Pd/C (10%, 0.5 g) in methanol (20 mL). The mixture was refluxed for 20 min, cooled to room temperature and diluted with dichloromethane (20 mL). The catalyst was filtered off and the filtrate was concentrated under reduced pressure to give a white solid material, which was crystallised from 50% ethanol/water to yield 680 mg (77%) of compound 25. δH (DMSO-d6) 8.12, (1H, s 8-H), 8.09 (1H, s, 2-H), 7.43-7.24 (m, 9H, DMT), 6.90 (m, 4H, DMT), 5.97 (1H, s, 1′-H), 4.44 (1H, s, 2′-H), 4.33 (1H, s, 3′-H), 3.97 (1H, d, J 7.5, Bn), 3.91(1H, d, J 7.7), 3.74 (6H, s, DMT), 3.55 (1H, d, J 10.6). δc (DMSO-d6) 158.2, 156.6, 147.3, 146.1, 144.8, 137.1, 135.5, 135.3, 129.8, 127.9, 127.7, 126.8, 124.6, 113.3(DMT, hypoxantine), 87.1, 85.6, 79.3, 71.8, 70.5, 59.9 (ribose), 55.1 (DMT).

Workup

  1. temperatureThe mixture was refluxed for 20 min
  2. filtrationThe catalyst was filtered off
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. customto give a white solid material, which
  5. customwas crystallised from 50% ethanol/water

Sources & evidence

ORD record
ord-c46e19fe4ffb4c6f84e170128468b29c
Source dataset
uspto-grants-2003_10
Patent number
US06639059B1

Reaction notes

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