Glycine methyl ester hydrochloride → HCID 86608923, compound

HRID 2112405Notes

Reaction equation

HRID 2112405 reaction equation
Cl[C:2]1[C:3]2[C:10]([N+:11]([O-:13])=[O:12])=[CH:9][N:8]([C@@H:14]3[O:27][C@H:26]([CH2:28][O:29][C:30](=[O:32])[CH3:31])[C@@H:20]([O:21][C:22](=[O:25])[CH2:23][CH3:24])[C@H:15]3[O:16][C:17](=[O:19])[CH3:18])[C:4]=2[N:5]=[CH:6][N:7]=1.Cl.[CH3:34][O:35][C:36](=[O:39])[CH2:37][NH2:38].C[O-].[Na+]>CO>[CH3:34][O:35][C:36](=[O:39])[CH2:37][NH:38][C:2]1[C:3]2[C:10]([N+:11]([O-:13])=[O:12])=[CH:9][N:8]([C@@H:14]3[O:27][C@H:26]([CH2:28][O:29][C:30](=[O:32])[CH3:31])[C@@H:20]([O:21][C:22](=[O:25])[CH2:23][CH3:24])[C@H:15]3[O:16][C:17](=[O:19])[CH3:18])[C:4]=2[N:5]=[CH:6][N:7]=1

Participants

5

Reactant 3

HCID 122755Glycine methyl ester hydrochlorideHCID 10942334Sodium MethoxideHCID 86608921HCID 86608921, compound

Product 1

HCID 86608923HCID 86608923, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
75 °C

Procedure

The compound from Step 3 (150 mg, 0.319 mmol) was dissolved in anhydrous MeOH (3 mL). Meanwhile glycine methylester mono hydrochloride (48 mg, 0.383 mmol) was neutralized with a 0.5M solution NaOMe (766 μl, 0.383 mmol) and this mixture was added to the methanolic solution containing nucleoside and the mixture was heated to 75° C. for 1.5 hours. Concentrated reaction in vacuo and purified on flash silica gel chromatography with a 0-5.0% MeOH gradient in DCM to afford 100 mg (60%).

Workup

  1. additionthis mixture was added to the methanolic solution
  2. concentrationConcentrated
  3. customreaction in vacuo
  4. custompurified on flash silica gel chromatography with a 0-5.0% MeOH gradient in DCM
  5. customto afford 100 mg (60%)

Sources & evidence

ORD record
ord-ccee8bafa3584ee780bb7e5219219d24
Source dataset
uspto-grants-2009_04
Patent number
US07524825B2

Reaction notes

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