Diisopropylethylamine → N-[(Benzhydryl-methyl-carbamoyl)-methyl]-3-phenyl-propionamide

HRID 2425172Notes

Reaction equation

HRID 2425172 reaction equation
[C:1]1([CH:7]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[NH:8][CH3:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:16]1([CH2:22][CH2:23][C:24]([NH:26][CH2:27][C:28]([OH:30])=O)=[O:25])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.CCN(C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F>C(#N)C>[CH:7]([N:8]([CH3:9])[C:28]([CH2:27][NH:26][C:24](=[O:25])[CH2:23][CH2:22][C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1)=[O:30])([C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1)[C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 152323PhenylpropionylglycineHCID 411467N-(Diphenylmethyl)methylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate

Product 1

HCID 59689161N-[(Benzhydryl-methyl-carbamoyl)-methyl]-3-phenyl-propionamideYield 46%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 2.0 mmol N-(diphenylmethyl)methylamine, 2.0 mmol (3-phenyl-propionylamino)-acetic acid (CA [56613-60-6]) and 6.0 mmol DIPEA in 10 ml of acetonitrile was treated with 2.2 mmol of TBTU. After 2 hours at room temperature, the reaction mixture was concentrated, diluted with water and extracted 3 times with ethyl acetate. The organic phase was dried and the residue purified by chromatography (SiO2; dichloromethane/methanol) to give the title compound as a slightly yellowish solid.

Workup

  1. concentrationthe reaction mixture was concentrated
  2. additiondiluted with water
  3. extractionextracted 3 times with ethyl acetate
  4. customThe organic phase was dried
  5. customthe residue purified by chromatography (SiO2; dichloromethane/methanol)

Sources & evidence

ORD record
ord-2fdbd749bb1c4520a0a2f62ab91029ef
Source dataset
uspto-grants-2011_06
Patent number
US07964645B2

Reaction notes

Loading…