Diisopropylethylamine → HCID 59356043, compound

HRID 660991Notes

Reaction equation

HRID 660991 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([O:8][CH2:9][C:10]2([C:15]3[S:19][C:18]([C:20](O)=[O:21])=[CH:17][CH:16]=3)[CH2:14][CH:13]=[CH:12][CH2:11]2)[CH:5]=[C:4]([CH3:23])[C:3]=1[C:24]1[CH:29]=[CH:28][C:27]([C:30]([F:33])([F:32])[F:31])=[CH:26][CH:25]=1.Cl.[CH3:35][O:36][C:37](=[O:41])[CH2:38][CH2:39][NH2:40].O.ON1C2C=CC=CC=2N=N1.C(N(CC)C(C)C)(C)C.Cl.CN(C)CCCN=C=NCC>CN(C=O)C.O>[CH3:35][O:36][C:37](=[O:41])[CH2:38][CH2:39][NH:40][C:20]([C:18]1[S:19][C:15]([C:10]2([CH2:9][O:8][C:6]3[CH:5]=[C:4]([CH3:23])[C:3]([C:24]4[CH:25]=[CH:26][C:27]([C:30]([F:32])([F:33])[F:31])=[CH:28][CH:29]=4)=[C:2]([CH3:1])[CH:7]=3)[CH2:11][CH:12]=[CH:13][CH2:14]2)=[CH:16][CH:17]=1)=[O:21]

Participants

8

Reactant 5

HCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 2734767Methyl 3-aminopropanoate hydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 67484499HCID 67484499, compound

Product 1

HCID 59356043HCID 59356043, compoundYield 65.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a mixture of 5-[1-(2,6-dimethyl-4′-trifluoromethyl-biphenyl-4-yloxymethyl)-cyclopent-3-enyl]-thiophene-2-carboxylic acid (0.204 g, 0.433 mmol), 3-amino-propionic acid methyl ester hydrochloride (0.0665 g, 0.476 mmol), and 1-hydroxybenzotriazole hydrate (HOBt, 0.0716 g, 0.530 mmol) in DMF (4.0 mL) is added N, N-diisopropylethylamine (0.240 mL, 1.37 mmol), then N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (EDCI, 0.106 g, 0.553 mmol) and stirred overnight. The reaction mixture is poured into H2O (10 mL) and extracted with EtOAc (3×10 mL). Combined organic extracts are washed with H2O, brine, dried over MgSO4, filtered, and concentrated. The residue is loaded onto silica gel and eluted using hexanes with an ethyl acetate gradient from 0% to 75% to provide 3-({5-[1-(2,6-dimethyl-4′-trifluoromethyl-biphenyl-4-yloxymethyl)-cyclopent-3-enyl]-thiophene-2-carbonyl}-amino)-propionic acid methyl ester (0.158 g, 65%) as a white foam. MS (ES): 556.3 [M−H]−.

Workup

  1. extractionextracted with EtOAc (3×10 mL)
  2. washCombined organic extracts are washed with H2O, brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. washeluted

Sources & evidence

ORD record
ord-1fbf0414caf14927816746eb47b11465
Source dataset
uspto-grants-2011_12
Patent number
US08084489B2

Reaction notes

Loading…