(+-)-Methionine → (1,2,3,4-tetrahydro-5-hydroxy-2-naphthyl)methyl N,N-diphenylcarbamate

HRID 963693Notes

Reaction equation

HRID 963693 reaction equation
[C:1]1([N:7]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[C:8](=[O:23])[O:9][CH2:10][CH:11]2[CH2:20][CH2:19][C:18]3[C:13](=[CH:14][CH:15]=[CH:16][C:17]=3[O:21]C)[CH2:12]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.NC(C(O)=O)CCSC>CS(O)(=O)=O>[C:24]1([N:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[C:8](=[O:23])[O:9][CH2:10][CH:11]2[CH2:20][CH2:19][C:18]3[C:13](=[CH:14][CH:15]=[CH:16][C:17]=3[OH:21])[CH2:12]2)[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1

Participants

4

Reactant 2

HCID 876(+-)-MethionineHCID 54050642(1,2,3,4-tetrahydro-5-methoxy-2-naphthyl)methyl N,N-diphenylcarbamate

Product 1

HCID 54103601(1,2,3,4-tetrahydro-5-hydroxy-2-naphthyl)methyl N,N-diphenylcarbamateYield 4.4%

Reagents, catalysts & solvents 1

HCID 6395Methanesulfonic AcidSolvent

Procedure

A suspension of (1,2,3,4-tetrahydro-5-methoxy-2-naphthyl)methyl N,N-diphenylcarbamate (1.93 g) and DL-methionine (7.43 g) in methanesulfonic acid (47.9 ml) was stirred at room temperature for 22 hours, then poured into ice water. The resulting mixture was extracted with ethyl acetate. The extract was washed successively with brine (twice), aqueous sodium bicarbonate and brine, dried over magnesium sulfate, and evaporated in vacuo. The residue was chromatographed (toluene-ethyl acetate) over silica gel to afford (1,2,3,4-tetrahydro-5-hydroxy-2-naphthyl)methyl N,N-diphenylcarbamate (82 mg) as yellow solids. mp: 96°-98° C.

Workup

  1. extractionThe resulting mixture was extracted with ethyl acetate
  2. washThe extract was washed successively with brine (twice), aqueous sodium bicarbonate and brine
  3. dry with materialdried over magnesium sulfate
  4. customevaporated in vacuo
  5. customThe residue was chromatographed (toluene-ethyl acetate) over silica gel

Sources & evidence

ORD record
ord-177fb8ff563d49ddb519bc102185efea
Source dataset
uspto-grants-1998_06
Patent number
US05763489

Reaction notes

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