Methanol → HCID 69946721, compound

HRID 844509Notes

Reaction equation

HRID 844509 reaction equation
C(N1C=CN=C1)(N1C=CN=C1)=O.[C:13]([OH:17])(=O)[CH2:14][CH3:15].[CH2:18]([NH:20][CH2:21][CH2:22][C:23]1[CH:28]=[CH:27][C:26]([OH:29])=[CH:25][CH:24]=1)[CH3:19].CO>O1CCCC1.C(OCC)(=O)C>[CH2:18]([N:20]([C:13](=[O:17])[CH2:14][CH3:15])[CH2:21][CH2:22][C:23]1[CH:24]=[CH:25][C:26]([OH:29])=[CH:27][CH:28]=1)[CH3:19]

Participants

7

Reactant 4

HCID 887MethanolHCID 1032Propionic AcidHCID 682631,1'-CarbonyldiimidazoleHCID 14777026HCID 14777026, compound

Product 1

HCID 69946721HCID 69946721, compoundYield 43.3%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of carbonyldiimidazole (14.13 g, 87.12 mmole) in tetrahydrofuran (109 ml) at 5° C., was added dropwise a solution of propionic acid (6.5 ml, 87.12 mmole) in tetrahydLrofuran (73 ml) over 30 minutes. After stirring for 20 minutes, N-ethyl tyramine (12.0 g, 72.6 mmole) in tetrahydlrofuran (73 ml) was added over 20 minutes. The reaction was allowed to warm to room temperature and stir for 4 hours. Methanol (7.3 ml) was added and stirring was continued for 30 minutes. The reaction was worked up by diluting with ethyl acetate and extracting with 1N hydrochloric acid, saturated sodium bicarbonate, then brine. The organic layer was dried over sodium sulfate, evaporated to dryness, and chromatographed on silica gel using a methylene chloride-methanol gradient to give N-ethyl,N-propionyl tyramine (6.95 g, 43%):

Workup

  1. stirringstir for 4 hours
  2. stirringstirring
  3. waitwas continued for 30 minutes
  4. extractionextracting with 1N hydrochloric acid, saturated sodium bicarbonate
  5. dry with materialThe organic layer was dried over sodium sulfate
  6. customevaporated to dryness
  7. customchromatographed on silica gel using a methylene chloride-methanol gradient

Sources & evidence

ORD record
ord-12a2a8b8c99940f6b8f65acb0cb2f165
Source dataset
uspto-grants-2002_04
Patent number
US06380213B1

Reaction notes

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