Chlorosulfamic acid → HCID 86607331, compound

HRID 552757Notes

Reaction equation

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

Participants

Reactant 2

HCID 24499Chlorosulfamic acid

HCID 67163569HCID 67163569, compound

Product 1

HCID 86607331HCID 86607331, compoundYield 29%

Procedure

Using essentially the same procedure as example 43, step f, ((2R,3S,5R)-5-[4-(benzylamino)-1H-pyrrolo[3,2-c]pyridin-1-yl]-3-{[tert-butyl(dimethyl)silyl]oxy}tetrahydrofuran-2-yl)methanol (0.0876 g, 0.193 mmol) was reacted with chlorosulfonamide, and the product was purified by flash chromatography (60 to 100% EtOAc/CH2Cl2) to afford the title compound (0.0300 g, 29%).

Workup

customthe product was purified by flash chromatography (60 to 100% EtOAc/CH2Cl2)

Sources & evidence

ORD record: ord-e75b022e696744f4ba6c20fce7d3b36b
Source dataset: uspto-grants-2011_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07951810B2

Reaction notes

Loading…