Ethanol → HCID 70170179, compound

HRID 1597464Notes

Reaction equation

HRID 1597464 reaction equation
C([C:8]1[CH:19]=[C:18](O)[CH:17]=[CH:16][C:9]=1[CH2:10][C@@H:11]([C:13]([OH:15])=[O:14])[NH2:12])C1C=CC=CC=1.[CH:21]1([NH:27][CH:28]2[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]2)[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]1.[C:34]([CH2:42][C:43]([CH3:45])=O)(=[O:41])[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1.[CH2:46]([OH:48])[CH3:47]>CO>[CH:28]1([NH:27][CH:21]2[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26]2)[CH2:29][CH2:30][CH2:31][CH2:32][CH2:33]1.[CH2:46]([O:48][C:18]1[CH:19]=[CH:8][C:9]([CH2:10][C@H:11]([NH:12][C:43]([CH3:45])=[CH:42][C:34](=[O:41])[C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[C:13]([OH:15])=[O:14])=[CH:16][CH:17]=1)[C:47]1[CH:25]=[CH:26][CH:21]=[CH:22][CH:23]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 7166BenzoylacetoneHCID 7582DicyclohexylamineHCID 57116221HCID 57116221, compound

Product 1

HCID 70170179HCID 70170179, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

A stirred mixture of 5.42 g (20 mmol) o-benzyl-L-tyrosine, 4.4 mL (22 mmol) dicyclohexylamine and 3.24 g (20 mmol) 1-benzoylacetone in 100 mL MeOH was refluxed for 24 h. 500 mL abs. ethanol was then added slowly to the solution and the MeOH was distilled out from the reaction flask with the same rate. The solution was then cooled to 0° C., stirred for 30 min, then filtered. The white solid was washed with 15 mL cold (−20° C.) abs. ethanol three times then dried to yield 7.60 g of the title compound: low resolution MS (FAB+) m/e 597 (MH+), 182 (DCAH+); Anal. (C38H48N2O4) Calcd. C, 76.47; H, 8.10; N, 4.69 Found C, 76.44; H, 8.16; N 4.63.

Workup

  1. temperaturewas refluxed for 24 h
  2. distillationthe MeOH was distilled out from the reaction flask with the same rate
  3. filtrationfiltered
  4. washThe white solid was washed with 15 mL cold (−20° C.) abs
  5. dry with materialethanol three times then dried

Sources & evidence

ORD record
ord-61b8ed09f161416a94d0c648eafb9ffc
Source dataset
uspto-grants-2001_09
Patent number
US06294580B1

Reaction notes

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