Chlorosulfamic acid → HCID 86607306, compound

HRID 552704Notes

Reaction equation

[CH3:1][C:2]1([CH3:32])[O:6][C@H:5]2[C@H:7]([N:12]3[CH:20]=[N:19][C:18]4[C:13]3=[N:14][CH:15]=[N:16][C:17]=4[C:21]3[CH:26]=[CH:25][CH:24]=[C:23]([N:27]4[CH:31]=[CH:30][CH:29]=[N:28]4)[CH:22]=3)[O:8][C@H:9]([CH2:10][OH:11])[C@H:4]2[O:3]1.Cl[S:34]([NH2:37])(=[O:36])=[O:35]>>[S:34](=[O:36])(=[O:35])([O:11][CH2:10][C@@H:9]1[C@@H:4]2[C@@H:5]([O:6][C:2]([CH3:32])([CH3:1])[O:3]2)[C@H:7]([N:12]2[CH:20]=[N:19][C:18]3[C:13]2=[N:14][CH:15]=[N:16][C:17]=3[C:21]2[CH:26]=[CH:25][CH:24]=[C:23]([N:27]3[CH:31]=[CH:30][CH:29]=[N:28]3)[CH:22]=2)[O:8]1)[NH2:37]

Participants

Reactant 2

HCID 24499Chlorosulfamic acid

HCID 67164781HCID 67164781, compound

Product 1

HCID 86607306HCID 86607306, compoundYield 88%

Procedure

Using essentially the same procedure as Example 43, step f, ((3aR,4R,6R,6aR)-2,2-dimethyl-6-{6-[3-(1H-pyrazol-1-yl)phenyl]-9H-purin-9-yl}tetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methanol (0.2 g, 0.46 mmol) was reacted with chlorosulfonamide, as described in Example 43, step f, and the product was purified by flash chromatography using 40-75% ethyl acetate/hexanes to give the title compound as a yellow solid (0.208, 88%).

Workup

customthe product was purified by flash chromatography

Sources & evidence

ORD record: ord-481f943fd264463ca56e40cd1dccfe47
Source dataset: uspto-grants-2011_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07951810B2

Reaction notes

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