1,2-Dichloroethane → 4-[2-{(2R)-2-[(1E,3S)-3-hydroxy-oct-1-enyl]-5-oxopyrrolidin-1-yl}ethyl)benzamide

HRID 28780

Reaction equation

HRID 28780 reaction equation
[OH:1][C@@H:2]([CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])/[CH:3]=[CH:4]/[C@H:5]1[CH2:9][CH2:8][C:7](=[O:10])[N:6]1[CH2:11][CH2:12][C:13]1[CH:21]=[CH:20][C:16]([C:17](O)=[O:18])=[CH:15][CH:14]=1.C(Cl)CCl.C1C=CC2N(O)N=[N:37]C=2C=1.[Cl-].N.CCN(C(C)C)C(C)C>CN(C=O)C>[OH:1][C@@H:2]([CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])/[CH:3]=[CH:4]/[C@H:5]1[CH2:9][CH2:8][C:7](=[O:10])[N:6]1[CH2:11][CH2:12][C:13]1[CH:21]=[CH:20][C:16]([C:17]([NH2:37])=[O:18])=[CH:15][CH:14]=1

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 102919634-(2-((R)-2-((S)-3-hydroxyoct-1-enyl)-5-oxopyrrolidin-1-yl)ethyl)benzoateHCID 20976574Ammonia chloride

Product 1

HCID 597883484-[2-{(2R)-2-[(1E,3S)-3-hydroxy-oct-1-enyl]-5-oxopyrrolidin-1-yl}ethyl)benzamideYield 97.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-[2-{(2R)-2-[(1E,3S)-3-hydroxy-oct-1-enyl]-5-oxopyrrolidin-1-yl}ethyl)benzoic acid (71.90 mg, 0.2 mmol) in DMF (1 mL) was added EDC (57.51 mg, 0.3 mmol), HOBt (40.54 mg, 0.3 mmol), ammonia chloride (21.40 mg, 0.4 mmoL) and DIPEA. The mixture was stirred for overnight. After evaporation of the solvent, the residue was purified through RP-HPLC using ACN and H2O/0.1% TFA to afford the desired product (70 mg) as a white solid. 1HNMR (CD3OD, ppm) δ 0.879 (m, 3H), 2.297 (br, 6H), 1.49 (m, 2H), 1.75 (m, 1H), 2.19 (m, 1H), 2.34 (m, 2H), 2.89 (m, 2H), 3.17 (m, 1H), 3.73 (t, J=7.0 Hz, 1H), 4.04 (t, J=6.2 Hz, 2H), 5.45 (dd, J=8.8 and 15.1 Hz, 1H), 5.66 (dd, J=6.6 and 15.1 Hz, 1H), 7.30 (d, J=7.7 Hz, 2H), 7.82 (d, J=7.7 Hz, 2H), (m/z): 381.4 (+Na+).

Workup

  1. customAfter evaporation of the solvent
  2. customthe residue was purified through RP-HPLC

Sources & evidence

ORD record
ord-751a7949d183477a8a004698247120a0
Source dataset
uspto-grants-2008_09
Patent number
US07419999B2

Linked notes

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