Chlorosulfamic acid → HCID 86607328, compound

HRID 552749Notes

Reaction equation

[Si:1]([O:8][C@@H:9]1[C@@H:13]([CH2:14][OH:15])[O:12][C@@H:11]([N:16]2[C:20]3[N:21]=[CH:22][N:23]=[C:24]([NH:25][C:26](=[O:33])[C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=4)[C:19]=3[CH:18]=[CH:17]2)[CH2:10]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].Cl[S:35]([NH2:38])(=[O:37])=[O:36]>>[S:35](=[O:37])(=[O:36])([O:15][CH2:14][C@@H:13]1[C@@H:9]([O:8][Si:1]([C:4]([CH3:5])([CH3:6])[CH3:7])([CH3:2])[CH3:3])[CH2:10][C@H:11]([N:16]2[C:20]3[N:21]=[CH:22][N:23]=[C:24]([NH:25][C:26](=[O:33])[C:27]4[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=4)[C:19]=3[CH:18]=[CH:17]2)[O:12]1)[NH2:38]

Participants

Reactant 2

HCID 24499Chlorosulfamic acid

HCID 21725232HCID 21725232, compound

Product 1

HCID 86607328HCID 86607328, compoundYield 48%

Procedure

Using essentially the same procedure as example 43 step f, N-{7-[(2R,4S,5R)-4-{[tert-butyl(dimethyl)silyl]oxy}-5-(hydroxymethyl)tetrahydrofuran-2-yl]-7H-pyrrolo[2,3-d]pyrimidin-4-yl}benzamide (0.524 g, 1.12 mmol) was reacted with chlorosulfonamide and the product was purified by flash chromatography (20 to 50% EtOAc/hexanes) to afford the title compound as a white foam (0.292 g, 48%).

Workup

customthe product was purified by flash chromatography (20 to 50% EtOAc/hexanes)

Sources & evidence

ORD record: ord-daa6d8a0eb8245bd8988a978da9abf5a
Source dataset: uspto-grants-2011_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07951810B2

Reaction notes

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