Ethylamine → HCID 117696650, compound

HRID 922557Notes

Reaction equation

HRID 922557 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([CH3:12])[C:9]([OH:11])=O)=[CH:4][CH:3]=1.CN(C(O[N:21]1N=N[C:23]2C=CC=C[C:22]1=2)=[N+](C)C)C.[B-](F)(F)(F)F.C(N)C>C1COCC1.CN(C=O)C>[CH2:22]([NH:21][C:9](=[O:11])[CH:8]([C:5]1[CH:4]=[CH:3][C:2]([OH:1])=[CH:7][CH:6]=1)[CH3:12])[CH3:23]

Participants

6

Reactant 3

HCID 6341EthylamineHCID 1025262-(4-Hydroxyphenyl)propionic acidHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate

Product 1

HCID 117696650HCID 117696650, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

To 4.00 g (24.1 mmol) 2-(4-hydroxyphenyl)propionic acid in 50 mL THF and 5 ml DMF are added 6.76 g (66.1 mmol) TEA and 8.50 g TBTU. The reaction mixture is stirred at r.t. for 5 min, then 36.1 ml (2 mold solution; 72.2 mmol) ethylamine are added. The reaction mixture is stirred at r.t. 5 h. The solvent is removed in vacuo and the crude product is purified by prep. HPLC-MS (ACN/H2O/NH4OH).

Workup

  1. stirringThe reaction mixture is stirred at r.t
  2. custom5 h
  3. customThe solvent is removed in vacuo
  4. customthe crude product is purified by prep

Sources & evidence

ORD record
ord-91f8d8bfa63e4372b6feedff920881b9
Source dataset
uspto-grants-2016_03
Patent number
US09278954B2

Reaction notes

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