Chlorosulfamic acid → HCID 58296154, compound

HRID 552752Notes

Reaction equation

[Br:1][C:2]1[CH:31]=[CH:30][C:5]([C:6]([NH:8][C:9]2[N:17]=[CH:16][N:15]=[C:14]3[C:10]=2[N:11]=[CH:12][N:13]3[C@H:18]2[C@H:25]3[C@H:21]([O:22]C(C)(C)[O:24]3)[C@@H:20]([CH2:28][OH:29])[O:19]2)=[O:7])=[CH:4][CH:3]=1.Cl[S:33]([NH2:36])(=[O:35])=[O:34]>>[S:33](=[O:35])(=[O:34])([O:29][CH2:28][C@@H:20]1[C@@H:21]([OH:22])[C@@H:25]([OH:24])[C@H:18]([N:13]2[CH:12]=[N:11][C:10]3[C:14]2=[N:15][CH:16]=[N:17][C:9]=3[NH:8][C:6](=[O:7])[C:5]2[CH:30]=[CH:31][C:2]([Br:1])=[CH:3][CH:4]=2)[O:19]1)[NH2:36]

Participants

Reactant 2

HCID 24499Chlorosulfamic acid

HCID 67164793HCID 67164793, compound

Product 1

HCID 58296154HCID 58296154, compoundYield 69%

Procedure

Using essentially the same procedure as example 39, step c, 4-bromo-N-{9-[(3aR,4R,6R,6aR)-6-(hydroxymethyl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl]-9H-purin-6-yl}benzamide (0.305 g, 0.622 mmol) was reacted with chlorosulfonamide, and the product was purified by flash chromatography (50 to 100% EtOAc/hexanes) to afford the title compound (0.243 g, 69%).

Workup

customthe product was purified by flash chromatography (50 to 100% EtOAc/hexanes)

Sources & evidence

ORD record: ord-5d6468b7850c4bfe92b14da44e502d63
Source dataset: uspto-grants-2011_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07951810B2

Reaction notes

Loading…