Water → HCID 67728932, compound

HRID 1956817Notes

Reaction equation

HRID 1956817 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:13]1=[N:14][CH:15]=[N:16][C:17]=2[NH2:21].O.[CH:23]1[C:35]2[CH:34]([CH2:36][O:37][C:38](ON3C(=O)CCC3=O)=[O:39])[C:33]3[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=3)[C:27]=2[CH:26]=[CH:25][CH:24]=1.C([O-])(O)=O.[Na+]>O1CCOCC1>[CH:23]1[C:35]2[CH:34]([CH2:36][O:37][C:38]([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:13]3=[N:14][CH:15]=[N:16][C:17]=4[NH2:21])=[O:39])[C:33]3[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=3)[C:27]=2[CH:26]=[CH:25][CH:24]=1

Participants

6

Reactant 4

HCID 962WaterHCID 134122N-(9-Fluorenylmethoxycarbonyloxy)succinimideHCID 516892Sodium BicarbonateHCID 13192091HCID 13192091, compound

Product 1

HCID 67728932HCID 67728932, compoundYield 82.8%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To 0.69 g (2.33 mmol) of 9-(2-amino-2-deoxy-β-D-glucopyranosyl)adenine was added 3.45 mL of H2O. To this solution was added a 28 mL 1,4-dioxane solution of 0.94 g (2.80 mmol) of N-(9-fluorenylmethoxycarbonyloxy)succinimide. This resulted in a cloudy mixture. To this system was added 0.13 g (1.50 mmol) of NaHCO3. This mixture was stirred for 12 h 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 18 h in 250 mL of Et2O and 250 ml of H2O. The suspension was then filtered and the solid dried in a vacuum oven for 2 days. Thus was obtained 1.0 g (82%) of the desired 9-[2-deoxy-2-[[(9H-fluoren-9-ylmethoxy)carbonyl]-amino]-β-D-glucopyranosyl]adenine 1H NMR: (DMSO-d6): adenine aromatic 8.19 (s, 1H), adenine aromatic 8.17 (s, 1H), anomeric H-1 6.60 (d, 1H), Fmoc-methine 4.17 (m, 1H). FAB-MS: m/z 519 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 18 h in 250 mL of Et2O
  5. filtrationThe suspension was then filtered
  6. customthe solid dried in a vacuum oven for 2 days

Sources & evidence

ORD record
ord-2da8c6dac48744a197a6373f3468b58b
Source dataset
uspto-grants-1998_07
Patent number
US05780607

Reaction notes

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