1-(Phenylmethyl) butanedioate → HCID 67133347, compound

HRID 2421803Notes

Reaction equation

HRID 2421803 reaction equation
[CH2:1]([O:8][C:9](=[O:15])[CH2:10][CH2:11][C:12]([OH:14])=[O:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:16][C@@:17]12[C@H:25](O)[CH2:24][C@@H:20]([C:21]1([CH3:23])[CH3:22])[CH2:19][CH2:18]2.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.Cl>CN(C1C=CN=CC=1)C.O1CCCC1>[C:9]([O:8][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)(=[O:15])[CH2:10][CH2:11][C:12]([O:14][C@@H:18]1[CH2:19][C@H:20]2[C:21]([CH3:23])([CH3:22])[C@:17]1([CH3:16])[CH2:25][CH2:24]2)=[O:13]

Participants

7

Reactant 4

HCID 87881-(Phenylmethyl) butanedioateHCID 757711-HydroxybenzotriazoleHCID 1201518[(1S)-endo]-(-)-BorneolHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 67133347HCID 67133347, compoundYield 62%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

In a 300 mL round bottom flask, fitted with reflux condenser, 4-(benzyloxy)-4-oxobutanoic acid (1.80 g, 1 eq., of Example 1) and anhydrous tetrahydrofuran (85 mL) were added. The reaction mixture was stirred under inert atmosphere and L-borneol (1.34 g, 1 eq.) was added, followed by the addition of HOBT (1.28 g, 1.1 eq.), EDC-HCl (1.81 g, 1.1 eq.) and DMAP (1.12 g, 1.1 eq). The reaction was heated in an oil bath at 50° C. for several hours until monitoring showed a substantial amount of product formation. The reaction mixture was filtered, concentrated and extracted with MTBE versus 1N HCl. The organic layer was washed with 1N HCl and brine, dried over MgSO4 and concentrated. The crude product was purified using column chromatography to give 1.83 g of a colorless oil (62%).

Workup

  1. customIn a 300 mL round bottom flask, fitted
  2. temperaturewith reflux condenser
  3. additionwas added
  4. filtrationThe reaction mixture was filtered
  5. concentrationconcentrated
  6. extractionextracted with MTBE versus 1N HCl
  7. washThe organic layer was washed with 1N HCl and brine
  8. dry with materialdried over MgSO4
  9. concentrationconcentrated
  10. customThe crude product was purified

Sources & evidence

ORD record
ord-0386c5d6613848e5a775663732feb6c9
Source dataset
uspto-grants-2011_06
Patent number
US07959958B2

Reaction notes

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