Water → HCID 178448377, compound

HRID 1940876Notes

Reaction equation

HRID 1940876 reaction equation
[CH:1]1[N:5]([CH2:6][O:7][CH:8]([CH2:11][OH:12])[CH2:9][OH:10])[C:4]2[N:13]=[C:14]([NH2:18])[N:15]=[C:16]([OH:17])[C:3]=2[N:2]=1.C(N(CC)CC)C.[CH3:26][CH:27]([C@H:29]([NH:33][C:34]([O:36][CH2:37][C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1)=[O:35])[C:30]([OH:32])=[O:31])[CH3:28].O>CN(C)C=O>[CH3:28][CH:27]([C@H:29]([NH:33][C:34]([O:36][CH2:37][C:38]1[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=1)=[O:35])[C:30]([OH:32])=[O:31])[CH3:26].[CH:1]1[N:5]([CH2:6][O:7][CH:8]([CH2:11][OH:12])[CH2:9][OH:10])[C:4]2[N:13]=[C:14]([NH2:18])[N:15]=[C:16]([OH:17])[C:3]=2[N:2]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 726987N-Carbobenzoxy-L-valineHCID 178418321HCID 178418321, compound

Product 1

HCID 178448377HCID 178448377, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a suspension of ganciclovir (5 gm) in dimethylformamide (30 ml) was added triethylamine (2.5 ml) and the Nα -Z-Valine-NCA (7.5 gm), and half hour later another portion (7.5 gm). After 3 hours from the initial addition, water was added and the reaction mixture was extracted with ethyl acetate. The organic phase was washed successively with sodium bisulfate solution (5%), water, sodium bicarbonate solution (5%), water, and brine, and then dried over sodium sulfate, filtered and evaporated. The residue was dissolved in toluene and precipitated by hexane addition. The solid was filtered washed with hexane, and dried under vacuum to give 15 gm of product.

Workup

  1. additionwas added
  2. extractionthe reaction mixture was extracted with ethyl acetate
  3. washThe organic phase was washed successively with sodium bisulfate solution (5%), water, sodium bicarbonate solution (5%), water, and brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. customevaporated
  7. dissolutionThe residue was dissolved in toluene
  8. customprecipitated by hexane addition
  9. filtrationThe solid was filtered
  10. washwashed with hexane
  11. customdried under vacuum

Sources & evidence

ORD record
ord-702c52f5e4e9487c90fc6baa9df3476b
Source dataset
uspto-grants-1997_12
Patent number
US05700936

Reaction notes

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