Methanol → HCID 70169472, compound

HRID 1597465Notes

Reaction equation

HRID 1597465 reaction equation
C([C:8]1[CH:19]=[C:18]([OH:20])[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]([CH:42]1[CH2:47][CH2:46][CH2:45][CH2:44][C:43]1=O)(=[O:41])[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1.[CH3:49]O>>[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.[C:34]([C:42]1[CH2:47][CH2:46][CH2:45][CH2:44][C:43]=1[NH:12][C@@H:11]([CH2:10][C:9]1[CH:8]=[CH:19][C:18]([O:20][CH2:49][C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=2)=[CH:17][CH:16]=1)[C:13]([OH:15])=[O:14])(=[O:41])[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1

Participants

5

Reactant 4

HCID 887MethanolHCID 7582DicyclohexylamineHCID 2756272-BenzoylcyclohexanoneHCID 57116221HCID 57116221, compound

Product 1

HCID 70169472HCID 70169472, compound

Conditions

Temperature
20 °C

Procedure

A stirred mixture of 1.35 g (5 mmol) o-benzyl-L-tyrosine, 1.0 mL (5 mmol) dicyclohexylamine and 1.01 g (5 mmol) 2-benzoylcyclohexanone (Denny, William A.; Cain, Bruce F.; J. Med. Chem. (1978), 21(5), 430-7.) in 25 mL MeOH was refluxed for 24 h. The solution was then cooled to 20° C., and the solvent was evaporated under reduced pressure. Purification of the residue by flash chromatography using Hexane/EtOAc (1:1) then EtOAc (neat), finally CHCl3/MeOH (10:1) as eluents resulted in 1.4 g of the of the title compound. 1H NMR (DMSO-d6, 400 MHz) δ 12.00 (d, 1H, J=8.4) 7.3 (m, 10H), 7.13 (d, 2H, J=8.5), 6.85 (d, 2H, J=8.5), 5.01 (s, 2H), 4.02 (m, 1H), 3.05 (m, 1H), 2.89 (m, 2H), 2.73 (dd, 1H, J=8.5, 13.7), 2.25 (m, 1H), 2.03 (m, 3H) 1.93 (m, 3H), 1.66 (m, 3H), 1.53 (d, 2H, J=12.3), 1.30 (m, 2H), 1.20 (m, 12H), 1.03 m (2H); low resolution MS (ESP+) m/e 456 (MH+).

Workup

  1. temperaturewas refluxed for 24 h
  2. customthe solvent was evaporated under reduced pressure
  3. customPurification of the residue by flash chromatography

Sources & evidence

ORD record
ord-aa306593022e4795b82f7116eb547a97
Source dataset
uspto-grants-2001_09
Patent number
US06294580B1

Reaction notes

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