L-Methionine → HCID 23462915, compound

HRID 2286416Notes

Reaction equation

HRID 2286416 reaction equation
[Cl:1][C:2]1[C:7]2[CH2:8][CH2:9][N:10]([CH3:13])[CH2:11][CH2:12][C:6]=2[C:5]([S:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[C:4]([O:21][CH3:22])[C:3]=1[O:23]C.CS(O)(=O)=O.N[C@H](C(O)=O)CCSC>>[Cl:1][C:2]1[C:7]2[CH2:8][CH2:9][N:10]([CH3:13])[CH2:11][CH2:12][C:6]=2[C:5]([S:14][C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)=[C:4]([O:21][CH3:22])[C:3]=1[OH:23]

Participants

4

Reactant 3

HCID 6137L-MethionineHCID 6395Methanesulfonic AcidHCID 12789229HCID 12789229, compound

Product 1

HCID 23462915HCID 23462915, compound

Procedure

To a solution of 0.8 g. (0.0022 mole) of 9-chloro-7,8-dimethoxy-3-methyl-6-phenylthio-2,3,4,5-tetrahydro-1H-3-benzazepine (prepared as in Example 15) in 10 ml. of methylsulfonic acid at room temperature is added 0.35 g. (0.0023 mole) of solid methionine all at once and the mixture is stirred for 4 hours. The reaction mixture is quenched in ice/water and made basic (pH 7.5) with concentrated ammonium hydroxide. The basic solution is extracted with methylene chloride and washed with saturated sodium chloride solution. The organic layer is dried and evaporated in vacuo to leave 9-chloro-8-hydroxy-7-methoxy-3-methyl-6-phenylthio-2,3,4,5-tetrahydro-1H-3-benzazepine.

Workup

  1. customThe reaction mixture is quenched in ice/water
  2. extractionThe basic solution is extracted with methylene chloride
  3. washwashed with saturated sodium chloride solution
  4. customThe organic layer is dried
  5. customevaporated in vacuo

Sources & evidence

ORD record
ord-a4e809f9aa914d09b258ac59c1c59444
Source dataset
uspto-grants-1981_05
Patent number
US04265890

Reaction notes

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