Acrylic Acid → HCID 86655436, compound

HRID 1746477Notes

Reaction equation

HRID 1746477 reaction equation
C(N(CC)CC)C.Cl.[NH2:9][C@H:10]([C:21]([O:23][CH3:24])=[O:22])[CH2:11][C:12]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[NH:14][CH:13]=1.[C:25](O)(=[O:28])[CH:26]=[CH2:27].C1CCC(N=C=NC2CCCCC2)CC1>C(Cl)Cl.C(Cl)(Cl)Cl>[C:25]([NH:9][C@H:10]([C:21]([O:23][CH3:24])=[O:22])[CH2:11][C:12]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[NH:14][CH:13]=1)(=[O:28])[CH:26]=[CH2:27]

Participants

7

Reactant 4

HCID 6581Acrylic AcidHCID 8471TriethylamineHCID 10868DicyclohexylcarbodiimideHCID 2734891Methyl tryptophanate hydrochloride

Product 1

HCID 86655436HCID 86655436, compoundYield 28%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent

Procedure

Triethylamine (14 mL) was added to a chloroform (120 mL) solution of methyl L-tryptophanate hydrochloride (5.0 g) under ice-cooling, and further acrylic acid (1.6 mL) was added thereto. Next, a methylene chloride (30 mL) solution of DCC (4.9 g) was added dropwise to the mixture. The mixture was stirred at room temperature for 24 hours, and thereafter a half the volume of the solvent was distilled off under a reduced pressure, acetone was added to the residual mixture, and the mixture was allowed to stand in a freezer overnight. Triethylamine hydrochloride and DC urea were filtered off, the solvents of the filtrate was distilled off under a reduced pressure, and the residual oily product obtained was purified by silica gel column chromatography (BW-127ZH, chloroform:methanol=19:1), to give the captioned compound (1.5 g, 28%) as an oily product.

Workup

  1. temperaturecooling
  2. distillationa half the volume of the solvent was distilled off under a reduced pressure, acetone
  3. additionwas added to the residual mixture
  4. waitto stand in a freezer overnight
  5. filtrationTriethylamine hydrochloride and DC urea were filtered off
  6. distillationthe solvents of the filtrate was distilled off under a reduced pressure
  7. customthe residual oily product obtained
  8. customwas purified by silica gel column chromatography (BW-127ZH, chloroform:methanol=19:1)

Sources & evidence

ORD record
ord-4747f8035f25496aabf94370039ba808
Source dataset
uspto-grants-2015_10
Patent number
US09150510B2

Reaction notes

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