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

HRID 28780

反応式

HRID 28780 の反応式
[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

参加物

7

反応物 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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

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+).

後処理

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

出典と根拠

ORDレコード
ord-751a7949d183477a8a004698247120a0
出典データセット
uspto-grants-2008_09
特許番号
US07419999B2

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