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 458905Notes

Reaction equation

HRID 458905 reaction equation
[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

Participants

4

Reactant 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

Product 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-benzothiazepineYield 84.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

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.

Workup

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

Sources & evidence

ORD record
ord-b62bdec40f5540a08a6dd93b4a2f71cc
Source dataset
uspto-grants-2007_03
Patent number
US07192945B2

Reaction notes

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