Triethylamine → HCID 86607304, compound

HRID 552702Notes

Reaction equation

HRID 552702 reaction equation
[C:1]([O:4][C@H:5]1[C@H:9]([O:10][C:11](=[O:13])[CH3:12])[C@@H:8]([CH2:14][OH:15])[O:7][C@H:6]1[N:16]1[CH:24]=[N:23][C:22]2[C:17]1=[N:18][CH:19]=[N:20][C:21]=2[NH:25][C@@H:26]1[C:34]2[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=2)[CH2:28][CH2:27]1)(=[O:3])[CH3:2].C(N(CC)CC)C.Cl[S:43]([NH2:46])(=[O:45])=[O:44]>C(Cl)Cl.C(#N)C>[C:11]([O:10][C@H:9]1[C@H:5]([O:4][C:1](=[O:3])[CH3:2])[C@H:6]([N:16]2[CH:24]=[N:23][C:22]3[C:17]2=[N:18][CH:19]=[N:20][C:21]=3[NH:25][C@@H:26]2[C:34]3[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=3)[CH2:28][CH2:27]2)[O:7][C@@H:8]1[CH2:14][O:15][S:43]([NH2:46])(=[O:45])=[O:44])(=[O:13])[CH3:12]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 24499Chlorosulfamic acidHCID 86607303HCID 86607303, compound

Product 1

HCID 86607304HCID 86607304, compoundYield 48%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

(2R,3S,4R,5R)-2-{6-[(1S)-2,3-Dihydro-1H-inden-1-ylamino]-9H-purin-9-yl}-5-(hydroxymethyl)tetrahydrofuran-3,4-diyl diacetate (0.188 g, 0.40 mmol) was stirred in anhydrous methylene chloride (0.6 mL) cooled to 0° C. Triethylamine (0.081 mL, 0.80 mmol) was added followed by the dropwise addition of a 2 N solution of chlorosulfonamide in acetonitrile (0.6 mL). The yellow solution was concentrated after one hour. The residue was purified by column chromatography using 0-5% methanol/methylene chloride concentrated to give the title compound as a yellow solid (0.104 g, 48%).

Workup

  1. concentrationThe yellow solution was concentrated after one hour
  2. customThe residue was purified by column chromatography
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-4fe16beedf634bd18d157c1b8ef022b4
Source dataset
uspto-grants-2011_05
Patent number
US07951810B2

Reaction notes

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