Acetylglycine → HCID 10292555, compound

HRID 1793261Notes

Reaction equation

HRID 1793261 reaction equation
[NH2:1][CH2:2][C@:3]1([CH2:18][OH:19])[O:7][C@@H:6]([N:8]2[CH:16]=[C:14]([CH3:15])[C:12](=[O:13])[NH:11][C:9]2=[O:10])[CH2:5][C@@H:4]1[OH:17].[C:20]([NH:23][CH2:24][C:25](O)=[O:26])(=[O:22])[CH3:21].[B-](F)(F)(F)F.CN(C(ON1C(=O)CCC1=O)=[N+](C)C)C.C(N(C(C)C)CC)(C)C>CN(C)C=O>[C:20]([NH:23][CH2:24][C:25]([NH:1][CH2:2][C@:3]1([CH2:18][OH:19])[O:7][C@@H:6]([N:8]2[CH:16]=[C:14]([CH3:15])[C:12](=[O:13])[NH:11][C:9]2=[O:10])[CH2:5][C@@H:4]1[OH:17])=[O:26])(=[O:22])[CH3:21]

Participants

6

Reactant 4

HCID 10972AcetylglycineHCID 81531DiisopropylethylamineHCID 98575222-(2,5-Dioxopyrrolidin-1-yl)-1,1,3,3-tetramethylisouronium tetrafluoroborateHCID 22881721HCID 22881721, compound

Product 1

HCID 10292555HCID 10292555, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4′-C-(Aminomethyl)thymidine (4) (0.025 g, 0.1 mmol), N-acetylglycine (0.023 g, 0.2 mmol) and TSTU (0.09 g, 0.3 mmol) were dissolved in anhydrous N,N-dimethylformamide (1 mL) at ambient temperature. Diisopropylethylamine (0.065 g, 0.5 mmol, 0.087 mL) was then added and the reaction mixture stirred for 18 hours at ambient temperature. The solvent was then removed under vacuum and the residue re-dissolved in 9:1 dichloromethane:methanol and eluted through a flash silica gel column with 9:1 dichloromethane:methanol. The title compound (19) was obtained as an amorphous solid on removal of solvent from the appropriate fractions (0.023 g). δH(300 MHz, CD3OD) 7.78(1H, s, H-6), 6.26(1H, dd, H-1′), 4.48(1H, dd, H-3′), 3.83(2H, s, glycyl CH2), 3.60(2H, 2d, H-5′), 3.58(1H, d, 4′-C—CH2), 3.42(1H, d, 4′-C—CH2), 2.33(2H, m, H-2′), 2.00(3H, s, CH3CO), 1.86(3H, s, 5-CH3); ES +ve m/z 393(M+Na)+.

Workup

  1. customThe solvent was then removed under vacuum
  2. dissolutionthe residue re-dissolved in 9:1 dichloromethane
  3. washmethanol and eluted through a flash silica gel column with 9:1 dichloromethane

Sources & evidence

ORD record
ord-fb8b2ce4648d484bbd1870054f1bc6c7
Source dataset
uspto-grants-2006_07
Patent number
US07078499B2

Reaction notes

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