Dicyclohexylcarbodiimide → HCID 178427475, compound

HRID 978338Notes

Reaction equation

HRID 978338 reaction equation
CN1C(=O)N[C@H](C(O)=O)CC1=O.ON1C(=O)CCC1=O.C1(N=C=NC2CCCCC2)CCCCC1.FC(F)(F)C(O)=O.[S:43]([NH:53][C@H:54]([C:61]([N:63]1[CH2:70][CH2:69][CH2:68][C@H:64]1[C:65]([NH2:67])=[O:66])=[O:62])[CH2:55][C:56]1[N:60]=[CH:59][NH:58][CH:57]=1)([C:46]1[CH:52]=[CH:51][C:49]([CH3:50])=[CH:48][CH:47]=1)(=[O:45])=[O:44]>CN(C)C=O.C(N(CC)CC)C>[S:43]([NH:53][C@H:54]([C:61]([N:63]1[CH2:70][CH2:69][CH2:68][C@H:64]1[C:65]([NH2:67])=[O:66])=[O:62])[CH2:55][C:56]1[N:60]=[CH:59][NH:58][CH:57]=1)([C:46]1[CH:47]=[CH:48][C:49]([CH3:50])=[CH:51][CH:52]=1)(=[O:44])=[O:45]

Participants

7

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 80170N-HydroxysuccinimideHCID 13507105(4S)-1-Methyl-2,6-dioxohexahydropyrimidine-4-carboxylic acidHCID 178427476HCID 178427476, compound

Product 1

HCID 178427475HCID 178427475, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Procedure

516 mg of 1-methyl-L-4,5-dihydroorotic acid and 345 mg of N-hydroxysuccinimide are dissolved in 9 ml of dimethylformamide, and 680 mg of dicyclohexylcarbodiimide are added thereto at 0° to 5° C. The mixture is stirred at the same temperature for 40 minutes and at room temperature for 80 minutes. 1.6 g of Nim -tosyl-L-histidyl-L-prolinamide trifluoroacetate (Bull. Chem. Soc. Jap., 49, 1595(1976)) and 0.5 ml of triethylamine added to the mixture and stirred at 10° C. for one day. After the reaction, the mixture is concentrated under reduced pressure, and the residue is dissolved in 30 ml of chloroform. Insoluble materials are filtered off, and the filtrate is washed with water and dried. After the mixture is concentrated under reduced pressure, the residue is purified by silica gel column chlomatography (solvent; chloroform:ethyl acetate:methanol=5:4:2). whereby 1.2 g of (1-methyl-L-4,5-dihydroorotyl)-nim -tosyl-L-histidyl-L-prolinamide are obtained as powder.

Workup

  1. customat 0° to 5° C
  2. stirringstirred at 10° C. for one day
  3. customAfter the reaction
  4. concentrationthe mixture is concentrated under reduced pressure
  5. dissolutionthe residue is dissolved in 30 ml of chloroform
  6. filtrationInsoluble materials are filtered off
  7. washthe filtrate is washed with water
  8. customdried
  9. concentrationAfter the mixture is concentrated under reduced pressure
  10. customthe residue is purified by silica gel column chlomatography (solvent; chloroform:ethyl acetate:methanol=5:4:2)

Sources & evidence

ORD record
ord-1fb841e3b810422aadd4c46f4be18110
Source dataset
uspto-grants-1987_05
Patent number
US04665056

Reaction notes

Loading…