Vinyl Chloride → HCID 9838506、化合物

HRID 2258573ノート

反応式

HRID 2258573 の反応式
[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([CH2:7][CH2:8][CH2:9][CH:10]2[CH2:13][CH2:14][NH2:15])=[CH:5][CH:4]=1.C(O)(=O)[C@H]([C@@H](C(O)=O)O)O.C=CCl.OP([O-])(O)=O.[K+].[CH3:35][O:36][CH2:37][C:38](Cl)=[O:39].[K+].[Br-]>C(Cl)(Cl)Cl.C(#N)C>[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([CH2:7][CH2:8][CH2:9][CH:10]2[CH2:13][CH2:14][NH:15][C:38](=[O:39])[CH2:37][O:36][CH3:35])=[CH:5][CH:4]=1

参加物

9

反応物 6

HCID 6338Vinyl ChlorideHCID 96623Methoxyacetyl chlorideHCID 253877Potassium BromideHCID 439655D-Tartaric acidHCID 516951Monobasic potassium phosphateHCID 219964722-(7-Methoxy-1,2,3,4-tetrahydronaphthalen-1-yl)ethan-1-amine

生成物 1

HCID 9838506HCID 9838506、化合物

試薬・触媒・溶媒 2

HCID 6212Chloroform溶媒HCID 6342Acetonitrile溶媒

実験手順

N-[2-(1,2,3,4-tetrahydro-7-methoxy naphthalen-1-yl)ethyl]amine was resolved according to the procedure described using D-tartaric acid and shown to have an enantomeric excess of 92% by HPLC analysis. The HPLC analyses were performed on a Ultron ES-OVM, 150×4.6 mm column using an isocratic mobile phase at 95/5 (A/B) where A is 20 mM KH2PO4, pH=3.0 and B is acetonitrile. This amine was converted into the amide according to General Procedure A using methoxyacetyl chloride. The final product was purified by recrystallization from EtOAc/hexane to give a white solid. m.p.=61°-63° C.; 1H NMR (300 MHz, CDCl3) δ6.96 (d, J=8 Hz, 1H), 6.67 (s, 1H), 6.65 (m, 1H), 6.51 (bs, 1H), 3.86 (s, 2H), 3.75 (s, 3H), 3.42 (m, 2H), 3.38 (s, 3H), 2.78 (m, 1H), 2.66 (bm, 2H), 1.97-1.76 (bm, 4H), 1.68-1.65 (m, 2H); 13C NMR (75 MHz, CDCl3) δ169.42, 157.55, 141.23, 130.01, 129.21, 113.34, 111.80, 71.99, 59.15, 55.28, 36.93, 36.45, 35.64, 28.72, 27.51, 20.00; IR (KBr) 1656 cm-1 ; MS (DCI) m/e 278 (MH); Analysis calc'd for C16H23N1O3 : C, 69.29; H, 8.36; N, 5.05; found: C, 69.15; H, 8.33; N, 4.89; [α] (25° C., 589 nm, CHCl3)=-8.33.

後処理

  1. customThe final product was purified by recrystallization from EtOAc/hexane
  2. customto give a white solid

出典と根拠

ORDレコード
ord-5037121c05174907b83ff6864f26a0be
出典データセット
uspto-grants-1997_08
特許番号
US05661186

反応ノート

読み込み中…