N-Carbobenzoxy-L-valine → HCID 136333677, compound

HRID 1871896Notes

Reaction equation

HRID 1871896 reaction equation
[C:1]([NH:11][C@H:12]([C:16]([OH:18])=[O:17])[CH:13]([CH3:15])[CH3:14])([O:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:2].[CH:19]1[N:23](COCCO)[C:22]2[N:29]=[C:30]([NH2:34])[N:31]=[C:32]([OH:33])[C:21]=2[N:20]=1>CN(C)C=O.CN(C)C1C=CN=CC=1>[O:3]([CH2:4][CH2:5][N:11]([C:1]([O:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:2])[C@H:12]([C:16]([O:18][N:23]1[CH:19]=[N:20][C:21]2[C:32](=[O:33])[NH:31][C:30]([NH2:34])=[N:29][C:22]1=2)=[O:17])[CH:13]([CH3:14])[CH3:15])[CH3:1]

Participants

5

Reactant 2

HCID 726987N-Carbobenzoxy-L-valineHCID 178508933HCID 178508933, compound

Product 1

HCID 136333677HCID 136333677, compoundYield 141.3%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolvent2×

Procedure

CBZ-L-valine (167 g) was dissolved in dimethylformamide (DMF) (750 ml) and cooled. A cold solution of N,N-dicyclohexyl-carbodiimide (DCC) (153.5 g) in DMF (266 ml) was added followed by acyclovir (111.7 g) in a single portion. 4-(dimethyl-amino)pyridine (9.4 g) was then added and the mixture stirred cold overnight. A white precipitate of the by-product was then removed by filtration. The filtrate was reduced in volume as before to give the title compound (215.3 g).

Workup

  1. temperaturecooled
  2. customA white precipitate of the by-product was then removed by filtration

Sources & evidence

ORD record
ord-c87cc2f1f2aa4860adfb6a1eb73c30e0
Source dataset
uspto-grants-2000_08
Patent number
US06107302

Reaction notes

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