Triethylamine → HCID 9830350, compound

HRID 2268354Notes

Reaction equation

HRID 2268354 reaction equation
[NH2:1][CH2:2][C:3]1[N:11]=[C:10]2[C:6]([N:7]=[CH:8][N:9]2[C@H:12]2[C@H:16]([OH:17])[C@H:15]([OH:18])[C@@H:14]([CH2:19][O:20][CH3:21])[O:13]2)=[C:5]([NH:22][CH2:23][CH:24]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[N:4]=1.[CH3:37][CH:38]([CH3:44])[CH2:39][S:40](Cl)(=[O:42])=[O:41].C(N(CC)CC)C>O1CCCC1>[OH:17][C@@H:16]1[C@H:15]([OH:18])[C@@H:14]([CH2:19][O:20][CH3:21])[O:13][C@H:12]1[N:9]1[CH:8]=[N:7][C:6]2[C:10]1=[N:11][C:3]([CH2:2][NH:1][S:40]([CH2:39][CH:38]([CH3:44])[CH3:37])(=[O:42])=[O:41])=[N:4][C:5]=2[NH:22][CH2:23][CH:24]([C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)[C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 1822361-Propanesulfonyl chloride, 2-methyl-2×HCID 9897827(2R,3R,4S,5R)-2-{2-(Aminomethyl)-6-[(2,2-diphenylethyl)amino]-9H-purin-9-yl}-5-(methoxymethyl)tetrahydro-3,4-furandiol

Product 1

HCID 9830350HCID 9830350, compoundYield 59.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

(2R,3R,4S,5R)-2-{2-(Aminomethyl)-6-[(2,2-diphenylethyl)amino]-9H-purin-9-yl}-5-(methoxymethyl)tetrahydro-3,4-furandiol (example 1) (300 mg, 0.61 mmol) was dissolved in dry tetrahydrofuran (20 ml) (using gentle heating), a solution of 2-methyl-1-propanesulphonyl chloride (50 mg, 0.32 mmol) in dry tetrahydrofuran (2.5 ml) added and the mixture stirred at room temperature for 18 hr under a nitrogen atmosphere. A solution of triethylamine (100 mg, 0.98 mmol) and 2-methyl-1-propanesulphonyl chloride (50 mg, 0.32 mmol) in dry tetrahydrofuran (5 ml) was added and the resulting mixture stirred for a further 5 hr. The solvent was then removed under reduced pressure and the residue purified by column chromatography on silica gel eluting with a solvent system of dichloromethane:methanol (97:3), to give the product as a foam (117 mg). MS: 611 (MH+).

Workup

  1. stirringthe resulting mixture stirred for a further 5 hr
  2. customThe solvent was then removed under reduced pressure
  3. customthe residue purified by column chromatography on silica gel eluting with a solvent system of dichloromethane:methanol (97:3)

Sources & evidence

ORD record
ord-0f4d569a20d84a0f812874f6116e02ba
Source dataset
uspto-grants-2001_12
Patent number
US06326359B1

Reaction notes

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