L-Methionine → HCID 69681544, compound

HRID 2181281Notes

Reaction equation

HRID 2181281 reaction equation
[CH3:1][N:2]([CH2:4][CH:5]1[CH2:11][CH2:10][O:9][C:8]2[CH:12]=[CH:13][CH:14]=[CH:15][C:7]=2[C:6]1([CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([O:24]C)[CH:19]=1)O)[CH3:3].COC1C=C(C=CC=1)C[Mg][Cl:33].CN(CC1CCOC2C=CC=CC=2C1=O)C.CS(O)(=O)=O.N[C@H](C(O)=O)CCSC.C(=O)(O)[O-].[Na+]>>[ClH:33].[CH3:1][N:2]([CH2:4][CH:5]1[CH2:11][CH2:10][O:9][C:8]2[CH:12]=[CH:13][CH:14]=[CH:15][C:7]=2/[C:6]/1=[CH:17]\[C:18]1[CH:19]=[C:20]([OH:24])[CH:21]=[CH:22][CH:23]=1)[CH3:3]

Participants

7

Reactant 6

HCID 6137L-MethionineHCID 6395Methanesulfonic AcidHCID 516892Sodium BicarbonateHCID 22485742HCID 22485742, compoundHCID 22485753HCID 22485753, compoundHCID 178490222HCID 178490222, compound

Product 1

HCID 69681544HCID 69681544, compound

Conditions

Temperature
40 °C

Procedure

A mixture of 4.78 g (4RS,5RS)-4-dimethylaminomethyl-5-(3-methoxybenzyl)-2,3,4,5-tetrahydrobenzo[b]oxepin-5-ol (prepared from 3-methoxybenzylmagnesium chloride and 4-dimethylaminomethyl-3,4-dihydro-2H-benzo[b]oxepin-5-one analogously to example 1, stage 1), 28 ml methanesulfonic acid and 3.20 g methionine was stirred at 40° C. for 4 days. Ice was then added and the mixture was cautiously rendered alkaline with sodium bicarbonate. It was extracted three times with 30 ml ethyl acetate each time and the extracts were washed with a saturated sodium chloride solution, dried over sodium sulfate and evaporated in vacuo. The crude product mixture obtained in this manner was separated by column chromatography with ethyl acetate and the individual compounds were converted into their hydrochlorides with trimethylchlorosilane/water in 2-butanone.

Workup

  1. additionIce was then added
  2. extractionIt was extracted three times with 30 ml ethyl acetate each time
  3. washthe extracts were washed with a saturated sodium chloride solution
  4. dry with materialdried over sodium sulfate
  5. customevaporated in vacuo

Sources & evidence

ORD record
ord-a93f7be2fb2d49ec99709107779296c4
Source dataset
uspto-grants-2005_05
Patent number
US06890952B2

Reaction notes

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