Chlorosulfamic acid → HCID 86607295, compound

HRID 552694Notes

Reaction equation

HRID 552694 reaction equation
[C:1]([O:4][C@H:5]1[CH2:9][C@H:8]([N:10]2[CH:18]=[N:17][C:16]3[C:11]2=[N:12][CH:13]=[N:14][C:15]=3[NH:19][C@@H:20]2[C:28]3[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=3)[CH2:22][CH2:21]2)[O:7][C@@H:6]1[CH2:29][OH:30])(=[O:3])[CH3:2].Cl[S:32]([NH2:35])(=[O:34])=[O:33]>>[C:1]([O:4][C@H:5]1[CH2:9][C@H:8]([N:10]2[CH:18]=[N:17][C:16]3[C:11]2=[N:12][CH:13]=[N:14][C:15]=3[NH:19][C@@H:20]2[C:28]3[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=3)[CH2:22][CH2:21]2)[O:7][C@@H:6]1[CH2:29][O:30][S:32]([NH2:35])(=[O:34])=[O:33])(=[O:3])[CH3:2]

Participants

3

Reactant 2

HCID 24499Chlorosulfamic acidHCID 67164798(2R,3S,5R)-5-{6-[(1S)-2,3-Dihydro-1H-inden-1-ylamino]-9H-purin-9-yl}-2-(hydroxymethyl)tetrahydrofuran-3-yl acetate

Product 1

HCID 86607295HCID 86607295, compoundYield 74%

Procedure

(2R,3S,5R)-5-{6-[(1S)-2,3-Dihydro-1H-inden-1-ylamino]-9H-purin-9-yl}-2-(hydroxymethyl)tetrahydrofuran-3-yl acetate (199 mg, 0.29 mmol) was treated with chlorosulfonamide as described in Example 39, step c. The product was purified by flash chromatography (0 to 5% MeOH/CH2Cl2) to afford 105 mg (74%) of the title compound.

Workup

  1. customThe product was purified by flash chromatography (0 to 5% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-449ea91d84d64f9e96bf2a0db3edf0e4
Source dataset
uspto-grants-2011_05
Patent number
US07951810B2

Reaction notes

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