Trifluoroacetic acid → HCID 86624976, compound

HRID 1668370Notes

Reaction equation

HRID 1668370 reaction equation
[CH2:1]([NH+:3]([CH2:6][CH3:7])[CH2:4][CH3:5])[CH3:2].C([O:15][C:16]1[CH:52]=[CH:51][CH:50]=[CH:49][C:17]=1[C:18]([NH:20][S:21]([O:24][CH2:25][C@H:26]1[O:30][C@@H:29]([N:31]2[C:40]3[N:39]=[CH:38][N:37]=[C:35]([NH2:36])[C:34]=3[N:33]=[CH:32]2)[C@H:28]([O:41][Si](C(C)(C)C)(C)C)[CH2:27]1)(=[O:23])=[O:22])=[O:19])C1C=CC=CC=1.C(O)(C(F)(F)F)=O>CO.[Pd]>[CH2:1]([NH+:3]([CH2:6][CH3:7])[CH2:4][CH3:5])[CH3:2].[OH:15][C:16]1[CH:52]=[CH:51][CH:50]=[CH:49][C:17]=1[C:18]([NH:20][S:21]([O:24][CH2:25][C@H:26]1[O:30][C@@H:29]([N:31]2[C:40]3[N:39]=[CH:38][N:37]=[C:35]([NH2:36])[C:34]=3[N:33]=[CH:32]2)[C@H:28]([OH:41])[CH2:27]1)(=[O:22])=[O:23])=[O:19]

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 131729075HCID 131729075, compound

Product 1

HCID 86624976HCID 86624976, compoundYield 53.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of 5′-O—[N-(2-benzyloxybenzoyl)sulfamoyl]-2′-O-tert-butyldimethylsilyl-3′-deoxyadenosine triethylammonium salt (70 mg, 0.092 mmol, 1.0 equiv) in MeOH (10 mL) was added 10% Pd/C (20 mg) and the reaction was stirred under H2 (1 atm) for 8 hours at room temperature. The reaction mixture was filtered through a plug of Celite and the residue was washed with MeOH (4×10 mL). The combined filtrates were concentrated and the crude obtained was treated with 80% aq TFA (2.0 mL) for 8 hours. The reaction was concentrated in vacuo. Purification by flash chromatography (10:90:1 MeOH/EtOAc/Et3N) afforded the title compound (27 mg, 53%) as a viscous oil: Rf 0.3 (1:4 MeOH/EtOAc); [α]20D −10 (c 0.28, MeOH); 1H NMR (600 MHz, CD3OD) δ 1.26 (t, J=7.2 Hz, 9H), 2.05-2.20 (m, 1H), 2.40-2.55 (m, 1H), 3.15 (q, J=7.2 Hz, 6H), 4.32 (dd, J=11.4, 4.2 Hz, 1H), 4.46 (d, J=11.4 Hz, 1H), 4.60-4.80 (m, 2H), 6.00 (s, 1H), 6.70-6.85 (m, 2H), 7.27 (t, J=7.2 Hz, 1H), 7.91 (d, J=7.8 Hz, 1H), 8.12 (s, 1H), 8.47 (s, 1H); 13C NMR (150 MHz, CD3OD) δ 9.3, 34.9, 47.9, 70.7, 76.9, 79.9, 92.9, 117.9, 119.3, 120.3, 120.7, 131.3, 134.3, 140.7, 150.2, 153.7, 157.3, 162.0, 174.9; HRMS (ESI+) calcd for C17H19N6O7S [M+H]+ 451.1030, found 451.1053 (error 5.1 ppm).

Workup

  1. filtrationThe reaction mixture was filtered through a plug of Celite
  2. washthe residue was washed with MeOH (4×10 mL)
  3. concentrationThe combined filtrates were concentrated
  4. customthe crude obtained
  5. concentrationThe reaction was concentrated in vacuo
  6. customPurification by flash chromatography (10:90:1 MeOH/EtOAc/Et3N)

Sources & evidence

ORD record
ord-4fa6241c018c4dc8a8686379a4fbd176
Source dataset
uspto-grants-2011_08
Patent number
US07989430B2

Reaction notes

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