Acetate → HCID 178476325, compound

HRID 357490Notes

Reaction equation

HRID 357490 reaction equation
[CH3:1][C:2]([O-:4])=[O:3].[CH:5]1[N:9]([CH2:10][O:11][CH:12]([CH2:15]O)[CH2:13][OH:14])[C:8]2[N:17]=[C:18]([NH2:22])[N:19]=[C:20]([OH:21])[C:7]=2[N:6]=1.[CH3:23][CH:24]([C@H:26]([NH:30][C:31]([O:33][CH2:34][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)=[O:32])[C:27]([OH:29])=[O:28])[CH3:25]>C(OC(C)C)(=O)C.CN(C)C=O.CN(C)C1C=CN=CC=1>[CH3:25][CH:24]([C@H:26]([NH:30][C:31]([O:33][CH2:34][C:35]1[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=1)=[O:32])[C:27]([OH:29])=[O:28])[CH3:23].[CH3:1][C:2]([O:4][CH2:15][CH:12]([O:11][CH2:10][N:9]1[C:8]2[NH:17][C:18]([NH2:22])=[N:19][C:20](=[O:21])[C:7]=2[N:6]=[CH:5]1)[CH2:13][OH:14])=[O:3]

Participants

7

Reactant 3

HCID 175AcetateHCID 726987N-Carbobenzoxy-L-valine2×HCID 178418321HCID 178418321, compound

Product 1

HCID 178476325HCID 178476325, compound

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolventHCID 7915Isopropyl AcetateSolvent2×

Procedure

To a solution of 4.0 g of the monoacetate of ganciclovir in 5 ml of isopropyl acetate and 5 ml of dimethylformamide was added 4.1 g of Z-valine-NCA and 0.08 g of 4-dimethylaminopyridine (DMAP). The solution was stirred for 3 hours at room temperature. An additional 0.8 g of Z-valine-NCA was added and stirring was continued for 1 hour. The solution was drowned with 75 ml of isopropyl acetate and stirred for 3 hours. The reaction mixture was then filtered and washed twice with 10 ml each of isopropyl acetate. The product was dried in a vacuum oven at ca. 500 mm of Hg (torr), (nitrogen sweep, 60°) overnight to give 5.6 g of Z-valine-ganciclovir monoacetate.

Workup

  1. stirringstirring
  2. waitwas continued for 1 hour
  3. stirringstirred for 3 hours
  4. filtrationThe reaction mixture was then filtered
  5. washwashed twice with 10 ml each of isopropyl acetate
  6. customThe product was dried in a vacuum oven at ca. 500 mm of Hg (torr), (nitrogen sweep, 60°) overnight

Sources & evidence

ORD record
ord-1a31587c30724ed298a5762b1d462445
Source dataset
uspto-grants-1998_11
Patent number
US05840890

Reaction notes

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