Triethylsilane → HCID 68867189, compound

HRID 1985184Notes

Reaction equation

HRID 1985184 reaction equation
[CH2:1]([O:3][C:4](=[O:50])[C:5]([CH3:49])([O:42][C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1)[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][CH2:14][CH2:15][CH:16]2[CH2:20][N:19]([CH2:21][C:22]3[CH:31]=[CH:30][C:29]4[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=4)[CH:23]=3)[C:18](=[O:32])[N:17]2CC2C=CC(OC)=CC=2)=[CH:9][CH:8]=1)[CH3:2].C([SiH](CC)CC)C>FC(F)(F)C(O)=O.O>[CH2:1]([O:3][C:4](=[O:50])[C:5]([CH3:49])([O:42][C:43]1[CH:44]=[CH:45][CH:46]=[CH:47][CH:48]=1)[CH2:6][C:7]1[CH:8]=[CH:9][C:10]([O:13][CH2:14][CH2:15][CH:16]2[CH2:20][N:19]([CH2:21][C:22]3[CH:31]=[CH:30][C:29]4[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=4)[CH:23]=3)[C:18](=[O:32])[NH:17]2)=[CH:11][CH:12]=1)[CH3:2]

Participants

5

Reactant 2

HCID 12052TriethylsilaneHCID 68866833HCID 68866833, compound

Product 1

HCID 68867189HCID 68867189, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of 3-(4-{2-[3-(4-methoxy-benzyl)-1-naphthalen-2-ylmethyl-2-oxo-imidazolidin-4-yl]-ethoxy}-phenyl)-2-methyl-2-phenoxy-propionic acid ethyl ester (1.54 g, 2.29 mmol) and triethylsilane (0.53 g, 4.56 mmol) in trifluroacetic acid (40 mL) is stirred at room temperature under N2 for 4 hours. The reaction mixture is diluted with water and extracted with EtOAc. The organic layer is dried and the solvent removed in vacuo to afford crude product that is purified by flash chromatography using 3:1 then 1:1 hexanes:acetone to afford 1.25 g (100%) 2-methyl-3-{4-[2-(1-naphthalen-2-ylmethyl-2-oxo-imidazolidin-4-yl]-ethoxy)-phenyl}-2-phenoxy-propionic acid ethyl ester. The diastereomeric mixture could be separated by chiral HPLC (2:3 IPA:heptane mobile phase, 14 mL/min, 225 nm) to afford >99% de 2-methyl-3-{4-[2-(1-naphthalen-2-ylmethyl-2-oxo-imidazolidin-4-yl)-ethoxy]-phenyl}-2-phenoxy-propionic acid ethyl esters. Rf=0.19 (1:1 acetone:hexanes). 1H NMR. MS (ES+) Calc'd for C34H37N2O5 (M+1) 553. Found m/z 553 (100%).

Workup

  1. extractionextracted with EtOAc
  2. customThe organic layer is dried
  3. customthe solvent removed in vacuo
  4. customto afford crude product that
  5. customis purified by flash chromatography

Sources & evidence

ORD record
ord-e8aef795e97c406ba0b716aae1c6f9b2
Source dataset
uspto-grants-2009_06
Patent number
US07544812B2

Reaction notes

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