Iodoethane → HCID 58904534, compound

HRID 1292742Notes

Reaction equation

HRID 1292742 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].[C:32](#N)[CH3:33].Cl[Si](C)(C)C.C(I)C>O>[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[CH2:32][CH3:33])[C:8]([OH:10])=[O:9]

Participants

6

Reactant 4

HCID 6340IodoethaneHCID 6342AcetonitrileHCID 6397ChlorotrimethylsilaneHCID 58904496HCID 58904496, compound

Product 1

HCID 58904534HCID 58904534, compoundYield 27.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

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 acetonitrile (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 ethyliodide (95 μl, 1.19 mmol) is added. Stirring at 55° C. is continued for another 16 h before water is added (about 200 μl). The solvent is removed under reduced pressure and the crude product is purified by prep. HPLC on Rp-C18 silica gel to furnish (±)-(S*)-(3,5-dimethoxy-phenoxy)-((1S*)-2-ethyl-1-phenyl-1,2,3,4-tetrahydro-isoquinolin-1-yl)-acetic acid (58 mg) as a white solid. LC-MS2: tR=4.20 min, [M+1]+=448.39, [M−1]−=446.34.

Workup

  1. additionis added
  2. additionis added
  3. additionis added (about 200 μl)
  4. customThe solvent is removed under reduced pressure
  5. customthe crude product is purified by prep

Sources & evidence

ORD record
ord-b2f7cfeb0d1e46a49784699a65193ff6
Source dataset
uspto-grants-2007_07
Patent number
US07238685B2

Reaction notes

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