(+-)-Methionine → HCID 14424031, compound

HRID 620175Notes

Reaction equation

HRID 620175 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:14]2[CH:15]=[C:16]([CH2:18][CH2:19][C:20]3[CH:25]=[CH:24][C:23]([O:26]C)=[CH:22][CH:21]=3)[S:17][C:13]=2[N:12]2[C:28]([CH3:31])=[N:29][N:30]=[C:11]2[CH2:10][N:9]=1.NC(C(O)=O)CCSC.C(=O)([O-])O.[Na+]>CS(O)(=O)=O>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:14]2[CH:15]=[C:16]([CH2:18][CH2:19][C:20]3[CH:25]=[CH:24][C:23]([OH:26])=[CH:22][CH:21]=3)[S:17][C:13]=2[N:12]2[C:28]([CH3:31])=[N:29][N:30]=[C:11]2[CH2:10][N:9]=1

Participants

5

Reactant 3

HCID 876(+-)-MethionineHCID 516892Sodium BicarbonateHCID 14424030HCID 14424030, compound

Product 1

HCID 14424031HCID 14424031, compoundYield 61.9%

Reagents, catalysts & solvents 1

HCID 6395Methanesulfonic AcidSolvent

Procedure

A mixture of 1.5 g of thienotriazolodiazepine compound obtained in Example 4 and 5 g of DL-methionine in 100 ml of methanesulfonic acid is allowed to stand at room temperature for 24 hours. The mixture is poured into 300 ml of ice-water, neutrarized with an aqueous sodium hydrogencarbonate solution and extracted with ethyl acetate. The organic layer is washed with a saturated sodium chloride solution and dried over anhydrous magnesium sulfate. After separating by filtration, the filtrate is concentrated to precipitate colorless crystals. The crystals are collected by filtration, washed with isopropyl ether and dried to give 0.9 g of 4-(2-chlorophenyl)-2-[2-(4-hydroxyphenyl)ethyl]-9-methyl-6H-thieno[3,2-f][1,2,4]triazolo[4,3-a][1,4]diazepine, melting at 100°-100° C.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer is washed with a saturated sodium chloride solution
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customAfter separating by filtration
  5. concentrationthe filtrate is concentrated
  6. customto precipitate colorless crystals
  7. filtrationThe crystals are collected by filtration
  8. washwashed with isopropyl ether
  9. customdried

Sources & evidence

ORD record
ord-585556d9f0354fa69cbcf81038a35075
Source dataset
uspto-grants-1989_04
Patent number
US04820703

Reaction notes

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