Diisopropylcarbodiimide → HCID 68309694, compound

HRID 1048848Notes

Reaction equation

HRID 1048848 reaction equation
[CH2:1]([N:8]1[C:13](=[O:14])[CH2:12][O:11][CH2:10][CH:9]1[C:15]([OH:17])=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1C=CC2N(O)N=NC=2C=1.CC(C)N=C=NC(C)C.[C:37]1([C@H:47]([NH2:49])[CH3:48])[C:46]2[C:41](=[CH:42][CH:43]=[CH:44][CH:45]=2)[CH:40]=[CH:39][CH:38]=1>ClCCl>[CH2:1]([N:8]1[C:13](=[O:14])[CH2:12][O:11][CH2:10][CH:9]1[C:15]([NH:49][C@@H:47]([C:37]1[C:46]2[C:41](=[CH:42][CH:43]=[CH:44][CH:45]=2)[CH:40]=[CH:39][CH:38]=1)[CH3:48])=[O:17])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 12734DiisopropylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 2724264(+)-1-(1-Naphthyl)ethylamineHCID 13543370HCID 13543370, compound

Product 1

HCID 68309694HCID 68309694, compoundYield 60.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 4-benzyl-5-oxomorpholine-3-carboxylic acid (Organic and Bio-Organic Chemistry (1972-1999); (1985); 2577-2580) (500 mg, 2.12 mmole) in dichloromethane (15 mL), HOBt (430 mg, 3.19 mmole) and DIPC (287 μL, 3.19 mmole) were added at room temperature. The reaction mixture was stirred for 15 min, then (R)-1-(naphthalen-1-yl)ethanamine (400 μL, 2.57 mmole) was added to the reaction mixture and stirred overnight. Solid separated out was filtered, washed with dichloromethane (2×15 mL), filtrate collected and washed with brine solution (2×15 mL) and DM water. The organic layer was concentrated to get crude amide and which was further purified by flash chromatography (n-Hexane:ethyl acetate, 8:3) to get title compound (500 mg). m/z 389.2

Workup

  1. stirringstirred overnight
  2. customSolid separated out
  3. filtrationwas filtered
  4. washwashed with dichloromethane (2×15 mL), filtrate
  5. customcollected
  6. washwashed with brine solution (2×15 mL) and DM water
  7. concentrationThe organic layer was concentrated
  8. customto get crude amide and which
  9. customwas further purified by flash chromatography (n-Hexane:ethyl acetate, 8:3)

Sources & evidence

ORD record
ord-529186db08f249099d389417d75b0c35
Source dataset
uspto-grants-2016_07
Patent number
US09382216B2

Reaction notes

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