Acetic Acid → HCID 18336830, compound

HRID 2297665Notes

Reaction equation

HRID 2297665 reaction equation
[Cl:1][C:2]1[N:10]=[CH:9][N:8]=[C:7]2[C:3]=1[N:4]=[CH:5][N:6]2[C@H:11]1[C@@H:15]2[O:16][C:17]([CH3:20])([CH3:19])[O:18][C@H:14]2[C@@H:13]([C:21]([NH:23][CH2:24][CH:25]([OH:27])[CH3:26])=[O:22])[O:12]1.C(O)(=O)C.[Cr](O[Cr]([O-])(=O)=O)([O-])(=O)=O.[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1.C(O)(C)C>ClCCl.C(OCC)(=O)C>[Cl:1][C:2]1[N:10]=[CH:9][N:8]=[C:7]2[C:3]=1[N:4]=[CH:5][N:6]2[C@H:11]1[C@@H:15]2[O:16][C:17]([CH3:20])([CH3:19])[O:18][C@H:14]2[C@@H:13]([C:21]([NH:23][CH2:24][C:25](=[O:27])[CH3:26])=[O:22])[O:12]1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 3776IsopropanolHCID 2724130Cornforth reagentHCID 86588179HCID 86588179, compound

Product 1

HCID 18336830HCID 18336830, compoundYield 70.1%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

To a mixture of (3aR,4S,6R,6aR)-6-(6-chloro-9H-purin-9-yl)-N-(2-hydroxypropyl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxole-4-carboxamide (6.60 g) and powdered 4 Å molecular sieves (10 g) in dichloromethane (165 ml) at 0° C., was added acetic acid (3.0 ml) followed by the portionwise addition of pyridinium dichromate (9.36 g). The mixture was stirred at 0° C. for 15 min and then at 20° C. for 2 hours. Isopropanol (10 ml) was added and the mixture stirred for 15 min. Silica gel (Merck 9385, 9.9 g) and ethyl acetate (165 ml) were added and the reaction stirred for a further 15 min. The mixture was filtered through celite and the filter cake washed with ethyl acetate (300 ml). The filtrate was evaporated in vacuo to give a brown solid. Purification by flash chromatography on silica gel, eluting with dichloromethane:methanol (100:3) gave a light brown foam. Further purification by chromatography on silica gel (Merck 9385), eluting with ethyl acetate followed by ethyl acetate:methanol (100:2) gave the title compound as a white foam (4.6 g).

Workup

  1. customat 0° C.
  2. waitat 20° C. for 2 hours
  3. stirringthe mixture stirred for 15 min
  4. stirringthe reaction stirred for a further 15 min
  5. filtrationThe mixture was filtered through celite
  6. washthe filter cake washed with ethyl acetate (300 ml)
  7. customThe filtrate was evaporated in vacuo
  8. customto give a brown solid
  9. customPurification by flash chromatography on silica gel
  10. washeluting with dichloromethane:methanol (100:3)
  11. customgave a light brown foam
  12. customFurther purification by chromatography on silica gel (Merck 9385)
  13. washeluting with ethyl acetate

Sources & evidence

ORD record
ord-749ac3a641404f62a3a6690a625237d5
Source dataset
uspto-grants-2002_12
Patent number
US06492348B1

Reaction notes

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