Acetic Acid → Eicosa-5,8,11,14-tetraenoic acid (4-chloro-benzyl)-(2,4-dichloro-phenyl)amide

HRID 392605

반응식

HRID 392605 반응식
[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=O)=[CH:4][CH:3]=1.[Cl:10][C:11]1[CH:17]=[C:16]([Cl:18])[CH:15]=[CH:14][C:12]=1[NH2:13].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(O)(=O)C.[C:37](O)(=[O:57])[CH2:38][CH2:39][CH2:40]/[CH:41]=[CH:42]\[CH2:43]/[CH:44]=[CH:45]\[CH2:46]/[CH:47]=[CH:48]\[CH2:49]/[CH:50]=[CH:51]\[CH2:52][CH2:53][CH2:54][CH2:55][CH3:56].C(Cl)(=O)C(Cl)=O>C(Cl)Cl.CN(C=O)C.ClCCCl>[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][N:13]([C:12]2[CH:14]=[CH:15][C:16]([Cl:18])=[CH:17][C:11]=2[Cl:10])[C:37](=[O:57])[CH2:38][CH2:39][CH2:40][CH:41]=[CH:42][CH2:43][CH:44]=[CH:45][CH2:46][CH:47]=[CH:48][CH2:49][CH:50]=[CH:51][CH2:52][CH2:53][CH2:54][CH2:55][CH3:56])=[CH:4][CH:3]=1

참가 물질

10

반응물 6

HCID 176Acetic AcidHCID 77264-ChlorobenzaldehydeHCID 111232,4-DichloroanilineHCID 65578Oxalyl chlorideHCID 444899Arachidonic AcidHCID 5049666Sodium triacetoxyborohydride

생성물 1

HCID 73022406Eicosa-5,8,11,14-tetraenoic acid (4-chloro-benzyl)-(2,4-dichloro-phenyl)amide수율 91%

시약·촉매·용매 3

HCID 6228Dimethylformamide촉매HCID 111,2-Dichloroethane용매HCID 6344Dichloromethane용매3회

실험 절차

Used the same procedure as above to synthesize 1.15 g (56%) of the desired amine from 4-chlorobenzaldehyde (1.0 g, 7.11 mmol), 2,4-dichloroaniline (1.27 g, 7.83 mmol), sodium triacetoxyborohydride (2.41 g, 11.38 mmol), acetic acid (0.41 mL, 7.11 mmol) and 1,2-dichloroethane (32 mL). 1H NMR δ4.36 (d, 2H, 5.8 Hz), 4.73 (br.s, 1H), 6.46 (d, 1H, 8.5 Hz), 7.03 (dd, 1H, 8.7, 2.2 Hz), 7.22-7.34 (m, 5H). Used the same procedure as above for generating the acid chloride and the subsequent condensation product: used arachidonic acid (234 mg, 0.77 mmol) in CH2Cl2 (5 mL) with oxalyl chloride (147 μL, 1.69 mmol) and DMF (2 drops). The acid chloride in CH2Cl2 (3 mL) was subsequently added to the respective amine (1.1 g, 3.84 mmol) in CH2Cl2 (5 mL). Isolated the desired product (O-2248; 400 mg, 91%) after purification by column chromatography (hexanes/EtOAc 97%/3% then 95%/5%) as a single rotomer. 1H NMR δ0.88 (t, 3H, 6.9 Hz), 1.24-1.41 (m, 6H), 1.67 (q, 2H, 7.1 Hz), 1.94 -2.05 (m, 6H), 2.75 (m, 6H), 4.03 (d, 1H, 14.3 Hz), 5.22-5.40 (m, 8H), 5.48 (d, 1H, 14.3 Hz), 6.70 (d, 1H, 8.5 Hz), 7.10-7.28 (m, 5H), 7.52 (d, 1H, 2.2 Hz). Anal. Calcd for C33H40NOCl3: C, 69.33; H, 7.06. Found: C, 69.17; H, 7.20.

출처 및 근거

ORD 기록
ord-1d24f0ebcd6746e7a155adb22639a804
출처 데이터셋
uspto-grants-2004_10
특허 번호
US06800770B2

연결된 노트

불러오는 중…