Triethylamine → HCID 178450008, compound

HRID 540388Notes

Reaction equation

HRID 540388 reaction equation
Cl.[NH2:2][C@H:3]([CH2:22][C:23]1[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[CH:25][CH:24]=1)[C:4]([N:6]1[CH2:9][C:8]([O:17][CH2:18][CH2:19][CH2:20][CH3:21])([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[CH3:16])[CH2:7]1)=[O:5].[CH3:31][C:32]1[N:36]=[CH:35][NH:34][C:33]=1[CH2:37][CH2:38][C:39](Cl)=[O:40].CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.C(N(CC)CC)C>CN(C)C=O.O>[CH2:18]([O:17][C:8]1([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[CH3:16])[CH2:7][N:6]([C:4](=[O:5])[C@H:3]([NH:2][C:39](=[O:40])[CH2:38][CH2:37][C:33]2[NH:34][CH:35]=[N:36][C:32]=2[CH3:31])[CH2:22][C:23]2[CH:24]=[CH:25][C:26]([O:29][CH3:30])=[CH:27][CH:28]=2)[CH2:9]1)[CH2:19][CH2:20][CH3:21]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 66988286(R)-2-amino-1-(3-butoxy-3-o-tolylazetidin-1-yl)-3-(4-methoxyphenyl)propan-1-one hydrochlorideHCID 178433263HCID 178433263, compound

Product 1

HCID 178450008HCID 178450008, compoundYield 86%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Procedure

146 mg (0.34 mmol) of (R)-2-amino-3-(4-methoxy-phenyl)-1-(3-butyloxy-3-o-tolylazetidin-1-yl)propan-1-one hydrochloride in solution in 2 ml of dimethylformamide are added to a solution of 64 mg (0.34 mmol) of 3-(5-methyl-3H-imidazol-4-yl)propanoic acid chloride, 119 mg (2.34 mmol) of TBTU and 0.15 ml (1.1 mmol) of triethylamine in 2 ml of dimethylformamide. The reaction mixture is stirred for 2 hours at ambient temperature. The reaction is stopped by adding 10 ml of water and then extracted with ethyl acetate. The organic phases are combined, washed with a 1N solution of sodium hydroxide and then a saturated solution of sodium chloride, and dried over sodium sulphate. After filtration, the solvents are evaporated off and the residue is then purified by silica gel chromatography (eluent 90/10 dichloromethane/methanol). 154 mg of N—[(R)-2-(3-butoxy-3-o-tolylazetidin-1-yl)-1-(4-methoxybenzyl)-2-oxoethyl]-3-(5-methyl-3H-imidazol-4-yl)propionamide are obtained in the form of a white powder with a yield of 86%.

Workup

  1. extractionextracted with ethyl acetate
  2. washwashed with a 1N solution of sodium hydroxide
  3. dry with materiala saturated solution of sodium chloride, and dried over sodium sulphate
  4. filtrationAfter filtration
  5. customthe solvents are evaporated off
  6. customthe residue is then purified by silica gel chromatography (eluent 90/10 dichloromethane/methanol)

Sources & evidence

ORD record
ord-72a76decc3f340d292567a4c013bed58
Source dataset
uspto-grants-2014_10
Patent number
US08871187B2

Reaction notes

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