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

HRID 28780

반응식

HRID 28780 반응식
[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

참가 물질

7

반응물 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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

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+).

후처리

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

출처 및 근거

ORD 기록
ord-751a7949d183477a8a004698247120a0
출처 데이터셋
uspto-grants-2008_09
특허 번호
US07419999B2

연결된 노트

불러오는 중…