Water → HCID 18336825, compound

HRID 2297683Notes

Reaction equation

HRID 2297683 reaction equation
[C:1]([O:4][C@@H:5]1[C@H:9]([O:10][C:11](=[O:13])[CH3:12])[C@@H:8]([C:14]#[CH:15])[O:7][C@H:6]1[N:16]1[CH:24]=[N:23][C:22]2[C:17]1=[N:18][CH:19]=[N:20][C:21]=2[NH:25][C:26]1[CH:31]=[CH:30][C:29]([Cl:32])=[CH:28][C:27]=1[F:33])(=[O:3])[CH3:2].[Br:34][C:35](Br)=[N:36][OH:37].C(=O)(O)[O-].[Na+].O>C(OCC)(=O)C>[C:1]([O:4][C@@H:5]1[C@H:9]([O:10][C:11](=[O:13])[CH3:12])[C@@H:8]([C:14]2[O:37][N:36]=[C:35]([Br:34])[CH:15]=2)[O:7][C@H:6]1[N:16]1[CH:24]=[N:23][C:22]2[C:17]1=[N:18][CH:19]=[N:20][C:21]=2[NH:25][C:26]1[CH:31]=[CH:30][C:29]([Cl:32])=[CH:28][C:27]=1[F:33])(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 516892Sodium BicarbonateHCID 27632191-bromo-N-hydroxymethanecarbonimidoyl bromideHCID 86588186HCID 86588186, compound

Product 1

HCID 18336825HCID 18336825, compoundYield 75.6%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

(2R,3R,4R,5R)-4-(acetyloxy)-2-[6-(4-chloro-2-fluoroanilino)-9H-purin-9-yl]-5-ethynyltetrahydrofuran-3-yl acetate (20 mg) was stirred at 22° C. with dibromoformaldoxime (12.5 mg), sodium bicarbonate (39 mg), water (0.075 ml) and ethyl acetate (1.5 ml) for 88 h. The mixture was partitioned between water (20 ml) and ethyl acetate (3×10 ml), the organic layers were washed with brine and evaporated in vacuo to give a brown gum (19 mg). Purification by chromatography on silica gel (Varian Bondelut cartridge), eluting with ethyl acetate:cyclohexane 20:80-80:20) gave the title compound as a colourless gum (16.8 mg).

Workup

  1. customThe mixture was partitioned between water (20 ml) and ethyl acetate (3×10 ml)
  2. washthe organic layers were washed with brine
  3. customevaporated in vacuo

Sources & evidence

ORD record
ord-fc422914ee21411ba1878997468160ff
Source dataset
uspto-grants-2002_12
Patent number
US06492348B1

Reaction notes

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