Triethylamine → HCID 69360617, compound

HRID 852547Notes

Reaction equation

HRID 852547 reaction equation
CC[N:3]([CH2:6][CH3:7])[CH2:4]C.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:15])C=CC=CC=1.[CH3:25][O:26][C:27](=[O:45])[C:28]1[CH:36]=[C:35]([O:37][CH2:38][C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=2)[CH:34]=C(C(O)=O)C=1.[CH3:46][Si:47]([CH3:52])([CH3:51])[CH2:48][CH2:49][OH:50]>C1(C)C=CC=CC=1>[CH3:25][O:26][C:27](=[O:45])[C:28]1[CH:7]=[C:6]([NH:3][C:4]([O:50][CH2:49][CH2:48][Si:47]([CH3:52])([CH3:51])[CH3:46])=[O:15])[CH:34]=[C:35]([O:37][CH2:38][C:39]2[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=2)[CH:36]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 180132-(Trimethylsilyl)ethanolHCID 199401P,P-Diphenylphosphinic azideHCID 214406211-Methyl 5-(phenylmethoxy)-1,3-benzenedicarboxylate

Product 1

HCID 69360617HCID 69360617, compoundYield 40%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
80 °C

Procedure

NEt3 (8.2 g, 81 mmol, 1.5 equiv) and diphenylphosphoryl azide (22.3 g, 81 mmol, 1.5 equiv) were added to a suspension of 5-benzyloxy-isophthalic acid monomethyl ester (D46) (15.5 g, 54.2 mmol, 1 equiv) in toluene (120 ml) and the resulting mixture heated at 80° C. for 3 h. 2-Trimethylsilylethanol (12.7 g, 108 mmol, 2 equiv) was added and the resulting mixture was refluxed for 4 h, cooled to room temperature and concentrated in vacuo. The residue was dissolved in EtOAc (300 ml) and the resulting solution was washed with 2N aqueous HCl solution (100 ml) followed by saturated aqueous NaHCO3 solution (100 ml), dried over MgSO4 and concentrated in vacuo. The residue was triturated with Et2O and iso-hexane to give 3-benzyloxy-5-(2-trimethylsilanyl-ethoxycarbonylamino)-benzoic acid methyl ester (D48) (8.5 g, 40%) as a white solid.

Workup

  1. temperaturethe resulting mixture was refluxed for 4 h
  2. temperaturecooled to room temperature
  3. concentrationconcentrated in vacuo
  4. dissolutionThe residue was dissolved in EtOAc (300 ml)
  5. washthe resulting solution was washed with 2N aqueous HCl solution (100 ml)
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated in vacuo
  8. customThe residue was triturated with Et2O and iso-hexane

Sources & evidence

ORD record
ord-ddd652013db6454eb30a1d553d0c9b5d
Source dataset
uspto-grants-2007_08
Patent number
US07253198B2

Reaction notes

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