Triethylamine → HCID 11638662, compound

HRID 1983843Notes

Reaction equation

HRID 1983843 reaction equation
[C:1]([C:5]1[CH:15]=[CH:14][C:8](/[CH:9]=[CH:10]/[C:11]([OH:13])=O)=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].Cl.[OH:17][C:18]1[CH:25]=[CH:24][C:21]([CH2:22][NH2:23])=[CH:20][C:19]=1[O:26][CH3:27].C(N(CC)CC)C.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1>CN(C=O)C.C(Cl)Cl.O>[C:1]([C:5]1[CH:6]=[CH:7][C:8](/[CH:9]=[CH:10]/[C:11]([NH:23][CH2:22][C:21]2[CH:24]=[CH:25][C:18]([OH:17])=[C:19]([O:26][CH3:27])[CH:20]=2)=[O:13])=[CH:14][CH:15]=1)([CH3:2])([CH3:3])[CH3:4]

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 165576Phenol, 4-(aminomethyl)-2-methoxy-, hydrochloride (1:1)HCID 7248394-(Tert-butyl)cinnamic acid

Product 1

HCID 11638662HCID 11638662, compoundYield 58.2%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

400 mg (1.96 mmol) of para-tert.-butyl-trans-cinnamic acid were dissolved at 5° C. in DMF (10 ml) together with 290 mg (1.94 mmol) of 4-hydroxy-3-methoxybenzyl-amine hydrochloride and 0.48 ml (6.50 mmol) of triethylamine. After the addition of a solution of 870 mg (1.97 mmol) of BOP in DCM (9 ml), stirring was continued for 16 h at RT. The reaction solution was then poured into water and extracted twice with a mixture of DIPE/EA (1:1). The combined organic phases were washed with 2M eq. hydrochloric acid and three times with 1 M eq. of sodium hydrogen carbonate solution and dried over magnesium sulfate. Follwing removal of the solvents and recrystallisation from DIPE, 384 mg (1.13 mmol, 58% of theoretical) of para-tert.-butyl-trans-N-(4-hydroxy-3-methoxybenzyl)-cinnamic acid amide were obtained.

Workup

  1. extractionextracted twice with a mixture of DIPE/EA (1:1)
  2. washThe combined organic phases were washed with 2M eq. hydrochloric acid and three times with 1 M
  3. dry with materialof sodium hydrogen carbonate solution and dried over magnesium sulfate
  4. customremoval of the solvents and recrystallisation from DIPE

Sources & evidence

ORD record
ord-361addb2836d47eb9633a7fd8a6c60ea
Source dataset
uspto-grants-2009_06
Patent number
US07541495B2

Reaction notes

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