Water → HCID 136351312, compound

HRID 1956819Notes

Reaction equation

HRID 1956819 reaction equation
[NH2:1][C@@H:2]1[C@@H:7]([OH:8])[C@H:6]([OH:9])[C@@H:5]([CH2:10][OH:11])[O:4][C@H:3]1[N:12]1[CH:20]=[N:19][C:18]2[C:17](=[O:21])[NH:16][C:15]([NH2:22])=[N:14][C:13]1=2.O.[CH:24]1[C:36]2[CH:35]([CH2:37][O:38][C:39](ON3C(=O)CCC3=O)=[O:40])[C:34]3[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=3)[C:28]=2[CH:27]=[CH:26][CH:25]=1.C([O-])(O)=O.[Na+]>O1CCOCC1>[CH:24]1[C:36]2[CH:35]([CH2:37][O:38][C:39]([NH:1][C@@H:2]3[C@@H:7]([OH:8])[C@H:6]([OH:9])[C@@H:5]([CH2:10][OH:11])[O:4][C@H:3]3[N:12]3[CH:20]=[N:19][C:18]4[C:17](=[O:21])[NH:16][C:15]([NH2:22])=[N:14][C:13]3=4)=[O:40])[C:34]3[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=3)[C:28]=2[CH:27]=[CH:26][CH:25]=1

Participants

6

Reactant 4

HCID 962WaterHCID 134122N-(9-Fluorenylmethoxycarbonyloxy)succinimideHCID 516892Sodium BicarbonateHCID 136351311HCID 136351311, compound

Product 1

HCID 136351312HCID 136351312, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To 3.31 g (10.61 mmol) of 9-(2-amino-2-deoxy-β-D-glucopyranosyl) guanine was added 72 mL of H2O. To this solution was added a 100 mL 1,4-dioxane solution containing 4.65 g (13.79 mmol) of N-(9-fluorenyl-methoxycarbonyloxy)succinimide. This resulted in a cloudy mixture. To this system was added 0.58 g (6.90 mmol) of NaHCO3. This mixture was stirred for 12 hours at room temperature. At this time, TLC indicated the consumption of starting material and the mixture was concentrated in vacuo to a dry residue. This residue was stirred for 3 hours in 310 mL of Et2O and 145 ml of H2O. The suspension was then filtered and the solid dried in a vacuum oven for 12 hours at 40° C. Thus was obtained 4.28 g (76%) of 9-(2-deoxy-2-[[(9H-fluoren-9-ylmethoxy)carbonyl]amino]-β-D-glucopyranosyl)guanine. 1H NMR: (DMSO-δ6): guanine H-8 7.72 (s, 1H), anomeric H-1 5.37 (d, 1H), Fmoc-methine 4.05 (m, 1H). FAB-MS: m/z 535 for (M+1)+.

Workup

  1. customThis resulted in a cloudy mixture
  2. customthe consumption of starting material
  3. concentrationthe mixture was concentrated in vacuo to a dry residue
  4. stirringThis residue was stirred for 3 hours in 310 mL of Et2O
  5. filtrationThe suspension was then filtered
  6. customthe solid dried in a vacuum oven for 12 hours at 40° C

Sources & evidence

ORD record
ord-1da25c5ee386443da90ca4a4ff3f70fa
Source dataset
uspto-grants-1998_07
Patent number
US05780607

Reaction notes

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