Acetic Anhydride → HCID 67165705, compound

HRID 552740Notes

Reaction equation

HRID 552740 reaction equation
[N:1]1([C@@H:10]2[O:14][C@H:13]([CH2:15][O:16][Si:17]([CH:24]([CH3:26])[CH3:25])([CH:21]([CH3:23])[CH3:22])[CH:18]([CH3:20])[CH3:19])[C@@H:12]([OH:27])[CH2:11]2)[C:9]2[CH:8]=[CH:7][N:6]=[CH:5][C:4]=2[CH:3]=[CH:2]1.[C:28](OC(=O)C)(=[O:30])[CH3:29]>CN(C1C=CN=CC=1)C.N1C=CC=CC=1>[C:28]([O:27][C@H:12]1[CH2:11][C@H:10]([N:1]2[C:9]3[CH:8]=[CH:7][N:6]=[CH:5][C:4]=3[CH:3]=[CH:2]2)[O:14][C@@H:13]1[CH2:15][O:16][Si:17]([CH:21]([CH3:23])[CH3:22])([CH:24]([CH3:26])[CH3:25])[CH:18]([CH3:20])[CH3:19])(=[O:30])[CH3:29]

Participants

5

Reactant 2

HCID 7918Acetic AnhydrideHCID 67164041HCID 67164041, compound

Product 1

HCID 67165705HCID 67165705, compoundYield 95%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1049PyridineSolvent

Procedure

To a solution of (2R,3S,5R)-5-(1H-pyrrolo[3,2-c]pyridin-1-yl)-2-{[(triisopropylsilyl)oxy]methyl}tetrahydrofuran-3-ol (0.487 g, 1.25 mmol) and a catalytic amount of DMAP in pyridine (1.6 mL) at 0° C. was added acetic anhydride (0.130 mL, 1.38 mmol) dropwise. The reaction was stirred overnight, concentrated, dissolved in EtOAc, washed with 1 M aq HCl (1×), water (1×) and brine (1×). The combined organics were washed with water (2×), dried (Na2SO4), filtered, and concentrated to give the title compound (0.464 g, 95%) which was used without further purification.

Workup

  1. concentrationconcentrated
  2. dissolutiondissolved in EtOAc
  3. washwashed with 1 M aq HCl (1×), water (1×) and brine (1×)
  4. washThe combined organics were washed with water (2×)
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-929ea00793d64ba68381714114cd1d62
Source dataset
uspto-grants-2011_05
Patent number
US07951810B2

Reaction notes

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