Trifluoroacetic acid → 1,1-Dioxo-3-butyl-3-ethyl-5-phenyl-7-bromo-8-(2-{N-[(R)-alpha-(carboxy)benzyl]carbamoyl}ethoxy)-2,3,4,5-tetrahydro-1,5-benzothiazepine

HRID 458905ノート

反応式

HRID 458905 の反応式
[O:1]=[S:2]1(=[O:46])[C:8]2[CH:9]=[C:10]([O:14][CH2:15][CH2:16][C:17](=[O:33])[NH:18][C@@H:19]([C:26]([O:28]C(C)(C)C)=[O:27])[C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[C:11]([Br:13])=[CH:12][C:7]=2[N:6]([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[CH2:5][C:4]([CH2:42][CH2:43][CH2:44][CH3:45])([CH2:40][CH3:41])[CH2:3]1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[O:46]=[S:2]1(=[O:1])[C:8]2[CH:9]=[C:10]([O:14][CH2:15][CH2:16][C:17](=[O:33])[NH:18][C@@H:19]([C:26]([OH:28])=[O:27])[C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[C:11]([Br:13])=[CH:12][C:7]=2[N:6]([C:34]2[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=2)[CH2:5][C:4]([CH2:42][CH2:43][CH2:44][CH3:45])([CH2:40][CH3:41])[CH2:3]1

参加物

4

反応物 2

HCID 6422Trifluoroacetic acidHCID 693605551,1-Dioxo-3-butyl-3-ethyl-5-phenyl-7-bromo-8-(2-{N-[(R)-alpha-(t-butoxycarbonyl)benzyl]carbamoyl}ethoxy)-2,3,4,5-tetrahydro-1,5-benzothiazepine

生成物 1

HCID 693615141,1-Dioxo-3-butyl-3-ethyl-5-phenyl-7-bromo-8-(2-{N-[(R)-alpha-(carboxy)benzyl]carbamoyl}ethoxy)-2,3,4,5-tetrahydro-1,5-benzothiazepine収率 84.5%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a solution of 1,1-dioxo-3-butyl-3-ethyl-5-phenyl-7-bromo-8-(2-{N-[(R)-α-(t-butoxycarbonyl)benzyl]carbamoyl}ethoxy)-2,3,4,5-tetrahydro-1,5-benzothiazepine (Method 90; 77 mg, 0.108 mmol) in DCM (3 ml) was added at 0° C. TFA (0.75 ml). The reaction mixture was stirred at room temperature for 2 h and 45 min. The solvent was evaporated under reduced pressure and the crude product was purified by preparative HPLC using MeCN and ammonium acetate buffer (40:60 to 50:50) as eluent to give the title compound 60 mg (82%). NMR (500 MHz, CD3OD) 0.75–0.85 (m, 6H), 1.0–1.25 (m, 4H), 1.40–1.64 (m, 4H), 2.75–2.90 (m, 2H), 3.26 (s, 2H), 3.50–3.90 (m, 2H), 4.30–4.41 (m, 2H), 5.43 (s, 1H), 6.99 (t, 1H), 7.05–7.13 (m, 3H), 7.23–7.34 (m, 5H), 7.45 (d, 2H), 7.52 (s, 1H); m/z 658.

後処理

  1. customThe solvent was evaporated under reduced pressure
  2. customthe crude product was purified by preparative HPLC

出典と根拠

ORDレコード
ord-b62bdec40f5540a08a6dd93b4a2f71cc
出典データセット
uspto-grants-2007_03
特許番号
US07192945B2

反応ノート

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