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 458905노트

반응식

HRID 458905 반응식
[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

참가 물질

4

반응물 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

생성물 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-benzothiazepine수율 84.5%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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.

후처리

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

출처 및 근거

ORD 기록
ord-b62bdec40f5540a08a6dd93b4a2f71cc
출처 데이터셋
uspto-grants-2007_03
특허 번호
US07192945B2

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