Diisopropylethylamine → HCID 68726450, compound

HRID 493172Notes

Reaction equation

HRID 493172 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[O:10][C:9]([C:11]([OH:13])=O)=[CH:8][C:7]=2[CH:14]=1.[CH3:15][C@H:16]1[O:21][C@@H:20]([CH3:22])[CH2:19][NH:18][CH2:17]1.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.C(N(C(C)C)C(C)C)C>C1COCC1>[CH3:22][C@H:20]1[O:21][C@@H:16]([CH3:15])[CH2:17][N:18]([C:11]([C:9]2[O:10][C:6]3[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:14][C:7]=3[CH:8]=2)=[O:13])[CH2:19]1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 2886385-Methoxybenzofuran-2-carboxylic acidHCID 6415002,6-Dimethylmorpholine, cis-

Product 1

HCID 68726450HCID 68726450, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In a flask were mixed together the above prepared 5-methoxy-benzofuran-2-carboxylic acid (0.428 g, 2.23 mmol), cis-2,6-dimethylmorpholine (0.308 g, 1.2 eq.), (benzotriazol-1-yloxy)-tris-(dimethylamino)phosphonium hexafluorophosphate (1.18 g, 1.2 eq.) and 2.4 eq. of N-ethyldiisopropylamine (0.915 mL) in 9 mL of abs. THF and allowed to react during one night at ambient temperature. Pouring onto crashed ice/AcOEt/NH4Cl-solution, twofold extraction with AcOEt, washing with water and brine, drying over magnesium sulfate, and evaporation of the solvents, followed by flash chromatography (SiO2, hexane/AcOEt=7/3 generated 0.614 g of the title compound as colorless oil.

Workup

  1. additionIn a flask were mixed together the
  2. customto react during one night at ambient temperature
  3. additionPouring
  4. extractionextraction with AcOEt
  5. washwashing with water and brine
  6. dry with materialdrying over magnesium sulfate, and evaporation of the solvents

Sources & evidence

ORD record
ord-7718fbc5a4ba49c0aabd25afb087b843
Source dataset
uspto-grants-2009_05
Patent number
US07534788B2

Reaction notes

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