Triethylamine → HCID 178498196、化合物

HRID 1056480ノート

反応式

HRID 1056480 の反応式
[OH:1][C:2]1[C:7]([CH:8]([CH3:10])[CH3:9])=[CH:6][C:5]([CH2:11][CH2:12][CH2:13][C:14]([OH:16])=O)=[CH:4][C:3]=1[CH:17]([CH3:19])[CH3:18].F[P-](F)(F)(F)(F)F.N1([PH+](N2CCCC2)N2CCCC2)CCCC1.[Cl-].[CH3:44][O:45][C:46]([C:48]1[CH:53]=[CH:52][C:51]([N:54]=[N:55][C:56]2[CH:61]=[CH:60][C:59]([CH2:62][NH3+:63])=[CH:58][CH:57]=2)=[CH:50][CH:49]=1)=[O:47].C(N(CC)CC)C>CN(C1C=CN=CC=1)C.C(Cl)Cl.C(Cl)(Cl)Cl.C(Cl)(Cl)Cl.CO>[OH:1][C:2]1[C:3]([CH:17]([CH3:19])[CH3:18])=[CH:4][C:5]([CH2:11][CH2:12][CH2:13][C:14]([NH:63][CH2:62][C:59]2[CH:58]=[CH:57][C:56](/[N:55]=[N:54]/[C:51]3[CH:52]=[CH:53][C:48]([C:46]([O:45][CH3:44])=[O:47])=[CH:49][CH:50]=3)=[CH:61][CH:60]=2)=[O:16])=[CH:6][C:7]=1[CH:8]([CH3:9])[CH3:10]

参加物

9

反応物 4

HCID 8471TriethylamineHCID 22226026Tripyrrolidinophosphonium hexafluorophosphateHCID 568512964-(4-Hydroxy-3,5-diisopropylphenyl)butanoic acidHCID 86695989(4-((4-(Methoxycarbonyl)phenyl)diazenyl)phenyl)methanaminium chloride

生成物 1

HCID 178498196HCID 178498196、化合物収率 57.4%

試薬・触媒・溶媒 4

HCID 142844-(Dimethylamino)pyridine触媒HCID 6212Chloroform溶媒HCID 6344Dichloromethane溶媒2 回HCID 21584188Chloroform methanol溶媒

実験手順

Acid 8 (164 mg, 1.00 mmol), benzotriazol-1-yloxy)tripyrrolidinophosphonium hexafluorophosphate (BOP, 884 mg, 2.00 mmol) and DMAP (12 mg, 0.10 mmol) were dissolved in methylene chloride (10 mL) and stirred at room temperature for 10 min. A solution of compound 4 (366 mg, 1.2 mmol) and triethylamine (505 mg, 5.0 mmol) in methylene chloride (15 mL) was added, and the reaction mixture was stirred at room temperature for 48 h. Aqueous work-up and chromatography on silica gel using chloroform and chloroform-methanol (3%) step-gradient as an eluent afforded pure 9 (296 mg, 57%) as orange crystals. 1H NMR (360 MHz, CDCl3): δ 8.18 (d, J=8.6 Hz, 2H), 7.93 (d, J=8.7 Hz, 2H), 7.91 (d, J=8.6 Hz, 2H), 7.43 (d, J=8.3 Hz, 2H), 6.85 (s, 2H), 5.83 (t, J=9.1 Hz, 1H), 4.73 (s, 1H), 4.53 (d, J=5.9 Hz, 2H), 3.96 (s, 3H), 3.11 (septet, J=6.9 Hz, 2H), 2.60 (t, J=7.8 Hz, 2H), 2.29 (t, J=7.6 Hz, 2H), 1.99 (q, J=7.6 Hz, 2H), 1.24 (d, J=6.9 Hz, 12H). 13C NMR (90.55 MHz, CDCl3): δ 173.23, 166.90, 155.42, 152.23, 148.52, 142.66, 133.99, 133.57, 132.17, 130.98, 128.85, 128.38, 123.87, 123.73, 123.01, 121.65, 120.13, 52.73, 43.56, 36.51, 35.45, 28.02, 27.51, 23.15. HRMS (m/z): [M+H]+ calcd. for C31H37N3O4 516.2857. found 516.2863.

後処理

  1. stirringthe reaction mixture was stirred at room temperature for 48 h

出典と根拠

ORDレコード
ord-a3e69b28956443acb418518a6b453f08
出典データセット
uspto-grants-2016_07
特許番号
US09399145B2

反応ノート

読み込み中…