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Methyl iodide → HCID 58904451, compound

HRID 1292741
Notes
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Reaction equation

HRID 1292741 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:27]=[C:28]([O:30][CH3:31])[CH:29]=1)[O:6][C@@H:7]([C@:11]1([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH2:14][CH2:13][NH:12]1)[C:8]([OH:10])=[O:9].[CH2:32]1COCC1.Cl[Si](C)(C)C.CI>CC(=O)OCC>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:27]=[C:28]([O:30][CH3:31])[CH:29]=1)[O:6][C@@H:7]([C@:11]1([C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH2:14][CH2:13][N:12]1[CH3:32])[C:8]([OH:10])=[O:9]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 6397ChlorotrimethylsilaneHCID 8028TetrahydrofuranHCID 58904496HCID 58904496, compound

Product 1

HCID 58904451HCID 58904451, compoundYield 67.2%

Reagents, catalysts & solvents 1

HCID 8857
Ethyl Acetate
Solvent

Conditions

Temperature
55 °C

Procedure

To a suspension of (±)-(S*)-(3,5-dimethoxy-phenoxy)-((1S*)-1-phenyl-1,2,3,4-tetrahydro-isoquinolin-1-yl)-acetic acid (200 mg, 0.477 mmol, Example 1) in THF (5 ml) Hünig's base (327 μl, 1.91 mmol) followed by chlorotrimethylsilane (72 μl, 0.572 mmol) is added. The mixture is stirred at 55° C. for 3 h before methyliodide (30 μl, 0.477 mmol) is added. Stirring at 55° C. is continued for another 16 h. The mixture is diluted with EA and extracted with water. The aqueous phase is acidified with 2 N HCl and extracted with EA. The EA-phase is dried over Na2SO4 and evaporated. The crude product is purified by prep. HPLC on Rp-C18-silica gel to give (±)-(S*)-(3,5-dimethoxy-phenoxy)-((1S*)-2-methyl-1-phenyl-1,2,3,4-tetrahydro-isoquinolin-1-yl)-acetic acid (139 mg) as a white powder. LC-MS2: tR=4.03 min, [M+1]+=434.34, [M−1]−=432.32.

Workup

  1. additionis added
  2. additionis added
  3. extractionextracted with water
  4. extractionextracted with EA
  5. dry with materialThe EA-phase is dried over Na2SO4
  6. customevaporated
  7. customThe crude product is purified by prep

Sources & evidence

ORD record
ord-ad96854889ed4d3cbd3cb1d0c8f48315
Source dataset
uspto-grants-2007_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07238685B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes