HCID 86624975, compound → HCID 86624974, compound

HRID 1668367Notes

Reaction equation

HRID 1668367 reaction equation
[CH2:1]([NH+:3]([CH2:6][CH3:7])[CH2:4][CH3:5])[CH3:2].[N:8]([C:11]1[N:12]([C:35]2[N:36]=[CH:37][N:38]=[C:39]([NH2:42])[C:40]=2[N:41]=1)[C@@H:13]1[O:34][C@H:18]([CH2:19][O:20][S:21](=[O:33])(=[O:32])[NH:22][C:23](=[O:31])[C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=2[OH:30])[C@@H:16]([OH:17])[C@H:14]1[OH:15])=[N+]=[N-]>CO.[Pd]>[CH2:1]([NH+:3]([CH2:6][CH3:7])[CH2:4][CH3:5])[CH3:2].[NH2:8][C:11]1[N:12]([C:35]2[N:36]=[CH:37][N:38]=[C:39]([NH2:42])[C:40]=2[N:41]=1)[C@@H:13]1[O:34][C@H:18]([CH2:19][O:20][S:21](=[O:33])(=[O:32])[NH:22][C:23](=[O:31])[C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=2[OH:30])[C@@H:16]([OH:17])[C@H:14]1[OH:15]

Participants

4

Reactant 1

HCID 86624975HCID 86624975, compound

Product 1

HCID 86624974HCID 86624974, compoundYield 73%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

8-Azido-5′-O—[N-(2-hydroxybenzoyl)sulfamoyl]adenosine triethylammonium salt (100 mg) was treated with Pd/C (5 mg) in MeOH (10 mL) under a H2 (1 atm) for 2 hours. The reaction was filtered thru Celite then concentrated in vacuo. Purification by flash chromatography (10:90 MeOH/EtOAc) afforded the title compound (69 mg, 73%) as a white solid: Rf 0.3 (20:80 MeOH/EtOAc); [α]20D −18.9 (c 1.0, MeOH); 1H NMR (600 MHz, CD3OD) δ 1.28 (t, J=6.6 Hz, 9H), 3.18 (q, J=7.2 Hz, 6H), 4.30 (d, J=2.4 Hz, 1H), 4.38-4.60 (m, 3H), 4.87-4.90 (ovlp m, 1H), 6.04 (d, J=7.2 Hz, 1H), 6.83 (q, J=9.0 Hz, 2H), 7.33 (q, J=7.2 Hz, 1H), 7.97 (d, J=7.8 Hz, 1H), 7.98 (s, 1H); 13C NMR (150 MHz, CD3OD) δ 9.35, 48.0, 69.7, 71.9, 72.0, 84.6, 88.6, 117.8, 118.0, 119.4, 120.6, 131.5, 134.6, 150.4, 151.1, 153.5, 153.8, 162.1, 175.2; HRMS (ESI+) calcd for C17H20N7O5S [M+H]+ 482.1088, found 482.1079 (error 1.8)

Workup

  1. filtrationThe reaction was filtered thru Celite
  2. concentrationthen concentrated in vacuo
  3. customPurification by flash chromatography (10:90 MeOH/EtOAc)

Sources & evidence

ORD record
ord-4c63b6c51d2d41ac8491561cf680c37d
Source dataset
uspto-grants-2011_08
Patent number
US07989430B2

Reaction notes

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