Diisopropylethylamine → HCID 59356031, compound

HRID 660988Notes

Reaction equation

HRID 660988 reaction equation
[CH2:1]([C:4]([C:28]1[S:32][C:31]([C:33](O)=[O:34])=[CH:30][CH:29]=1)([CH2:8][O:9][C:10]1[CH:15]=[C:14]([CH3:16])[C:13]([C:17]2[CH:22]=[CH:21][C:20]([C:23]([F:26])([F:25])[F:24])=[CH:19][CH:18]=2)=[C:12]([CH3:27])[CH:11]=1)[CH2:5][CH:6]=[CH2:7])[CH:2]=[CH2:3].Cl.[CH3:37][O:38][C:39](=[O:43])[CH2:40][CH2:41][NH2:42].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>[CH3:37][O:38][C:39](=[O:43])[CH2:40][CH2:41][NH:42][C:33]([C:31]1[S:32][C:28]([C:4]([CH2:5][CH:6]=[CH2:7])([CH2:8][O:9][C:10]2[CH:11]=[C:12]([CH3:27])[C:13]([C:17]3[CH:18]=[CH:19][C:20]([C:23]([F:24])([F:26])[F:25])=[CH:21][CH:22]=3)=[C:14]([CH3:16])[CH:15]=2)[CH2:1][CH:2]=[CH2:3])=[CH:29][CH:30]=1)=[O:34]

Participants

8

Reactant 5

HCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 2734767Methyl 3-aminopropanoate hydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 67485090HCID 67485090, compound

Product 1

HCID 59356031HCID 59356031, compoundYield 70%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a mixture of 5-[1-allyl-1-(2,6-dimethyl-4′-trifluoromethyl-biphenyl-4-yloxymethyl)-but-3-enyl]-thiophene-2-carboxylic acid (0.1695 g, 0.338 mmol), 3-amino-propionic acid methyl ester hydrochloride (0.0533 g, 0.382 mmol), and 1-hydroxybenzotriazole hydrate (HOBt, 0.0561 g, 0.415 mmol) in DMF (3.5 mL) is added N, N-diisopropylethylamine (0.175 mL, 1.00 mmol), then N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (EDCI, 0.0836 g, 0.436 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-allyl-1-(2,6-dimethyl-4′-trifluoromethyl-biphenyl-4-yloxymethyl)-but-3-enyl]-thiophene-2-carbonyl}-amino)-propionic acid methyl ester (0.138 g, 70%) as a white foam. MS (ES): 584.3 [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-db7fc69e08554e68aee3c301254e4387
Source dataset
uspto-grants-2011_12
Patent number
US08084489B2

Reaction notes

Loading…