Tetrabutylammonium Fluoride → HCID 86761378, compound

HRID 1668369Notes

Reaction equation

HRID 1668369 reaction equation
[Si]([O:8][C@@H:9]1[C@@H:13]([CH2:14][O:15][S:16](=[O:28])(=[O:27])[NH:17][C:18](=[O:26])[C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=2[OH:25])[O:12][C@@H:11]([N:29]2[C:38]3[N:37]=[CH:36][N:35]=[C:33]([NH2:34])[C:32]=3[N:31]=[CH:30]2)[CH2:10]1)(C(C)(C)C)(C)C.CC[CH2:41][CH2:42][N+:43](CCCC)([CH2:48][CH2:49]CC)[CH2:44][CH2:45]CC.[F-]>C1COCC1>[CH2:42]([NH+:43]([CH2:48][CH3:49])[CH2:44][CH3:45])[CH3:41].[OH:25][C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=1[C:18]([NH:17][S:16]([O:15][CH2:14][C@H:13]1[O:12][C@@H:11]([N:29]2[C:38]3[N:37]=[CH:36][N:35]=[C:33]([NH2:34])[C:32]=3[N:31]=[CH:30]2)[CH2:10][C@@H:9]1[OH:8])(=[O:27])=[O:28])=[O:26]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 16098537HCID 16098537, compound

Product 1

HCID 86761378HCID 86761378, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3′-O-tert-butyldimethylsilyl-2′-deoxy-5′-O—[N-(2-hydroxybenzoyl)sulfamoyl]-adenosine (10.5 mg, 0.018 mmol, 1.0 equiv) in THF (2.0 mL) was added TBAF (1.0 M solution in THF, 0.1 mL, 6.0 equiv) and the solution stirred 3 hours at room temperature. The reaction mixture was concentrated and purification of the residue by flash chromatography (65:35:1 EtOAc/MeOH/Et3N) afforded the title compound (5.1 mg, 50%): Rf 0.15 (3:1 EtOAc/MeOH); [α]20D −99 (c 0.25, CH3OH) 1H NMR (600 MHz, CD3OD) δ 1.29 (t, J=7.2 Hz, 9H), 2.44 (ddd, J=13.8, 5.4, 2.4 Hz, 1H), 2.70-2.90 (m, 1H), 3.18 (q, J=7.2 Hz, 6H), 4.24 (s, 1H), 4.32 (dd, J=11.4, 3.6 Hz, 1H), 4.35 (dd, J=10.8, 3.6 Hz, 1H), 4.62-4.70 (m, 1H), 6.50 (t, J=6.6 Hz, 1H), 6.75-6.84 (m, 2H), 7.29 (t, J=7.8 Hz, 1H), 7.93 (d, J=7.8 Hz, 1H), 8.16 (s, 1H), 8.50 (s, 1H); 13C NMR (150 MHz, CD3OD) δ 9.4, 41.6, 48.1, 70.0, 73.5, 85.9, 87.0, 118.0, 119.4, 120.3, 120.8, 131.5, 134.5, 141.3, 150.6, 153.9, 157.4, 162.2, 175.1; HRMS (ESI+) calcd for C17H19N6O7S [M+H]+ 451.1030, found 451.1014 (error 3.5 ppm).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. custompurification of the residue by flash chromatography (65:35:1 EtOAc/MeOH/Et3N)

Sources & evidence

ORD record
ord-fc71e993e215451ea885fd631368c803
Source dataset
uspto-grants-2011_08
Patent number
US07989430B2

Reaction notes

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