Triethylamine → HCID 86607297, compound

HRID 552696Notes

Reaction equation

HRID 552696 reaction equation
[C:1]([O:4][C@@H:5]1[CH2:9][C@@H:8]([CH2:10][OH:11])[O:7][C@H:6]1[N:12]1[CH:20]=[N:19][C:18]2[C:13]1=[N:14][CH:15]=[N:16][C:17]=2[NH:21][C@@H:22]1[C:30]2[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=2)[CH2:24][CH2:23]1)(=[O:3])[CH3:2].C(N(CC)CC)C.Cl[S:39]([NH2:42])(=[O:41])=[O:40]>CN(C=O)C.C(#N)C.CCOC(C)=O.O>[C:1]([O:4][C@@H:5]1[CH2:9][C@@H:8]([CH2:10][O:11][S:39](=[O:41])(=[O:40])[NH2:42])[O:7][C@H:6]1[N:12]1[CH:20]=[N:19][C:18]2[C:13]1=[N:14][CH:15]=[N:16][C:17]=2[NH:21][C@@H:22]1[C:30]2[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=2)[CH2:24][CH2:23]1)(=[O:3])[CH3:2]

Participants

8

Reactant 3

HCID 8471Triethylamine2×HCID 24499Chlorosulfamic acid2×HCID 67164635HCID 67164635, compound

Product 1

HCID 86607297HCID 86607297, compoundYield 52%

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (2R,3R,5S)-5-hydroxymethyl-2-[6-((S)-indan-1-ylamino)-purin-9-yl]tetrahydrofuran-3-yl acetate (0.20 mmol) and triethylamine (56 μL, 0.0.40 mmol) in DMF (3.3 mL) was added dropwise 150 μL of a 2M solution of the chlorosulfonamide in acetonitrile and the cloudy solution was stirred. Identical amounts of triethylamine and the chlorosulfonamide solution were added after 2.5 and 4 hours. The reaction was diluted with EtOAc and water, the layers were separated, and the aqueous layer was extracted with EtOAc (1×). The combined organic layers were washed with brine, dried over Na2SO4, filtered, and concentrated in vacuo. The crude material was purified by silica gel chromatography (0% to 10% MeOH/CH2Cl2) to afford 51 mg (52%) of the title compound.

Workup

  1. customthe layers were separated
  2. extractionthe aqueous layer was extracted with EtOAc (1×)
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe crude material was purified by silica gel chromatography (0% to 10% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-df0001a3ea0d4e48a4d0cb99151087bf
Source dataset
uspto-grants-2011_05
Patent number
US07951810B2

Reaction notes

Loading…