Triethylamine → 3-[4-(2-Benzyloxy-acetoxy)-phenyl]-2-{3-[4-(2-benzyloxy-acetoxy)-phenyl]propionyl amino}-propionic acid methyl ester

HRID 546367Notes

Reaction equation

HRID 546367 reaction equation
[CH3:1][O:2][C:3](=[O:25])[CH:4]([NH:13][C:14](=[O:24])[CH2:15][CH2:16][C:17]1[CH:22]=[CH:21][C:20]([OH:23])=[CH:19][CH:18]=1)[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([OH:12])=[CH:8][CH:7]=1.C(N([CH2:31][CH3:32])CC)C.[CH2:33]([O:40][CH2:41][C:42](Cl)=[O:43])[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1>CC(C)=O>[CH3:1][O:2][C:3](=[O:25])[CH:4]([NH:13][C:14](=[O:24])[CH2:15][CH2:16][C:17]1[CH:18]=[CH:19][C:20]([O:23][C:42](=[O:43])[CH2:41][O:40][CH2:33][C:32]2[CH:31]=[CH:36][CH:35]=[CH:34][CH:39]=2)=[CH:21][CH:22]=1)[CH2:5][C:6]1[CH:7]=[CH:8][C:9]([O:12][C:42](=[O:43])[CH2:41][O:40][CH2:33][C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)=[CH:10][CH:11]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 177085Benzyloxyacetyl chlorideHCID 118576273-(4-Hydroxy-phenyl)-2-[3-(4-hydroxy-phenyl)-propionylamino]-propionic acid methyl ester

Product 1

HCID 584275113-[4-(2-Benzyloxy-acetoxy)-phenyl]-2-{3-[4-(2-benzyloxy-acetoxy)-phenyl]propionyl amino}-propionic acid methyl ester

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of 3-(4-hydroxy-phenyl)-2-[3-(4-hydroxy-phenyl)-propionylamino]-propionic acid methyl ester 23 (10 grams, 29.15 mmol) and triethylamine (7.4 grams, 73.12 mmol) in anhydrous acetone (100 mL) at 0° C. is added dropwise benzyloxy acetyl chloride (11.8 grams, 63.95 mmol). The reaction mixture is stirred at room temperature for 10 hours. The resulting solids are filtered off. Acetone is distilled off, and water (100 mL) is added. The crude 25 is extracted into chloroform (2×100 mL), washed with 5% sodium bicarbonate (2×25 mL) and water (2×25 mL), dried over sodium sulphate, and distilled to give crude 25, which can be purified from appropriate solvent.

Workup

  1. filtrationThe resulting solids are filtered off
  2. distillationAcetone is distilled off
  3. additionwater (100 mL) is added
  4. extractionThe crude 25 is extracted into chloroform (2×100 mL)
  5. washwashed with 5% sodium bicarbonate (2×25 mL) and water (2×25 mL)
  6. dry with materialdried over sodium sulphate
  7. distillationdistilled
  8. customto give crude 25, which
  9. customcan be purified from appropriate solvent

Sources & evidence

ORD record
ord-3b44f127927a4a029b676f15e6e9cc20
Source dataset
uspto-grants-2011_05
Patent number
US07935843B2

Reaction notes

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