Methanesulfonyl chloride → 9-((1R,2S,3R,4S)-2,3-Dihydroxy-4-propionylamino-cyclopentyl)-6-(2,2-diphenyl-ethylamino)-9H-purine-2-carboxylic acid (2-methanesulfonylamino-ethyl)-amide

HRID 1882583Notes

Reaction equation

[NH2:1][CH2:2][CH2:3][NH:4][C:5]([C:7]1[N:15]=[C:14]2[C:10]([N:11]=[CH:12][N:13]2[C@@H:16]2[CH2:20][C@H:19]([NH:21][C:22](=[O:25])[CH2:23][CH3:24])[C@@H:18]([OH:26])[C@H:17]2[OH:27])=[C:9]([NH:28][CH2:29][CH:30]([C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)[C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[N:8]=1)=[O:6].[S:43](Cl)([CH3:46])(=[O:45])=[O:44]>C(Cl)(Cl)Cl.C(Cl)Cl>[CH3:46][S:43]([NH:1][CH2:2][CH2:3][NH:4][C:5]([C:7]1[N:15]=[C:14]2[C:10]([N:11]=[CH:12][N:13]2[C@@H:16]2[CH2:20][C@H:19]([NH:21][C:22](=[O:25])[CH2:23][CH3:24])[C@@H:18]([OH:26])[C@H:17]2[OH:27])=[C:9]([NH:28][CH2:29][CH:30]([C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)[C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[N:8]=1)=[O:6])(=[O:45])=[O:44]

Participants

Conditions

Temperature: 5 °C

Procedure

A solution of 9-((1R,2S,3R,4S)-2,3-dihydroxy-4-propionylamino-cyclopentyl)-6-(2,2-diphenyl-ethylamino)-9H-purine-2-carboxylic acid (2-amino-ethyl)-amide (0.01 g, 0.017 mmol) in chloroform (1 ml) is treated with mesyl chloride (1 ml of a 3 mg/ml solution in chloroform) and TEA (0.003 ml). After stirring at 5° C. for 1 hour, the reaction mixture is diluted with DCM and extracted with 1 M HCl. The organic portion is isolated and concentrated in vacuo to yield the title product. (MH+ 651.5)

Workup

extractionextracted with 1 M HCl
customThe organic portion is isolated
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-67a2d900012048188fbea926cfa73f7a
Source dataset: uspto-grants-2012_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08318750B2

Reaction notes

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