Triethylamine → HCID 23399151, compound

HRID 1062357Notes

Reaction equation

HRID 1062357 reaction equation
C(N1C=CN=C1)(N1C=CN=C1)=O.[C:13]1(/[CH:19]=[CH:20]/[CH:21]=[CH:22]/[C:23]([OH:25])=O)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(N(CC)CC)C.Cl.[NH2:34][CH2:35][CH2:36][S:37][CH2:38][CH2:39][C:40]([O:42][CH3:43])=[O:41]>O1CCCC1>[CH3:43][O:42][C:40](=[O:41])[CH2:39][CH2:38][S:37][CH2:36][CH2:35][NH:34][C:23](=[O:25])/[CH:22]=[CH:21]/[CH:20]=[CH:19]/[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 682631,1'-CarbonyldiimidazoleHCID 15495121552-94-9HCID 22287102HCID 22287102, compound

Product 1

HCID 23399151HCID 23399151, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1,1′-Carbonyldiimidazole (0.36 g, 2.2 mmol) was added to a solution of 5-phenyl-penta-2E,4E-dienoic acid (1/1) (0.35 g, 2 mmol) in dry tetrahydrofuran (10 ml) and the obtained mixture was stirred for 1 hour at ambient temperature. To the mixture triethylamine (0.30 g 3.0 mmol) and methyl 3-(2-amino-ethylsulfanyl)-propionate hydrochloride (2e) (2.2 mmol) were added and the resultant suspension was stirred for 6 hours at ambient temperature. The solvent was removed under reduced pressure, to the residue water (15 ml) was added and the precipitate was filtered off, washed with water and dried, to give the title product. Yield 67%, m.p. 58-60° C. 1H NMR (90 MHz, DMSO-d6) δ: 2.54-2.89 (6H, m, CH2); 2.96-3.45 (2H, m, CH2); 3.61 (3H, s, CH3); 6.14 (1H, d, J=14.5 Hz, CH); 6.81-7.16 (2H, m, CH—CH); 7.11-7.69 (6H, m, C6H5, CH); 8.18 (1H, t, J=5.4 Hz, NH).

Workup

  1. customThe solvent was removed under reduced pressure, to the residue water (15 ml)
  2. additionwas added
  3. filtrationthe precipitate was filtered off
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-d21b99ed556d414f81e40e9cdd5114a2
Source dataset
uspto-grants-2005_11
Patent number
US06960685B2

Reaction notes

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