Methionin AL → HCID 178447960, compound

HRID 1680975Notes

Reaction equation

HRID 1680975 reaction equation
N[C@H](C=O)CCSC.[CH2:9]([C@H:12]1[CH2:17][CH2:16][C@H:15]([CH2:18][CH2:19][CH:20]([C:26]([O:28]CC)=O)[C:21]([O:23]CC)=O)[CH2:14][CH2:13]1)[CH2:10][CH3:11].Cl.[F:32][C:33]1[CH:34]=[C:35]([CH:39]=[CH:40][C:41]=1[F:42])[C:36]([NH2:38])=[NH:37]>CO.Cl>[OH:23][C:21]1[C:20]([CH2:19][CH2:18][C@H:15]2[CH2:14][CH2:13][C@H:12]([CH2:9][CH2:10][CH3:11])[CH2:17][CH2:16]2)=[C:26]([OH:28])[N:37]=[C:36]([C:35]2[CH:39]=[CH:40][C:41]([F:42])=[C:33]([F:32])[CH:34]=2)[N:38]=1

Participants

6

Reactant 3

HCID 446793Methionin ALHCID 198078513,4-Difluorobenzene-1-carboximidamide--hydrogen chloride (1/1)HCID 178447965HCID 178447965, compound

Product 1

HCID 178447960HCID 178447960, compoundYield 94.2%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 887MethanolSolvent

Procedure

Metal sodium (0.3 g) was dissolved in anhydrous methanol (100 m(), followed by adding diethyl 2-(trans-4'-propylcyclohexyl)ethylmalonate (3.2 g) and 3,4-difluorobenzamidine hydrochloride (1.9 g) with stirring, reacting the mixture under reflux for 10 hours, thereafter cooling the reaction solution, pouring it in 6N HCl (100 ml) and ice (300 g), filtering off deposited yellow crystals, washing with water and drying crystals to obtain 4,6-dihydroxy-5-[2'-(trans-4"-propylcyclohexyl)ethyl]-2-(3,4-difluorophenyl)pyrimidine (3.5 g).

Workup

  1. temperatureunder reflux for 10 hours
  2. temperaturecooling the reaction solution
  3. filtrationice (300 g), filtering off
  4. washwashing with water
  5. customdrying crystals

Sources & evidence

ORD record
ord-cb5dd775a6894de1b507300a6cc953df
Source dataset
uspto-grants-1992_12
Patent number
US05167858

Reaction notes

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