Trifluoroacetic acid → HCID 67271991, compound

HRID 601710Notes

Reaction equation

HRID 601710 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:40]=[C:41]([F:43])[CH:42]=1)[CH2:5][C@H:6]1[C@@H:10]([C@H:11]2[CH2:20][C:19]3[C:14](=[C:15]([O:21][Si:22]([CH:29]([CH3:31])[CH3:30])([CH:26]([CH3:28])[CH3:27])[CH:23]([CH3:25])[CH3:24])[CH:16]=[CH:17][CH:18]=3)[CH2:13][N:12]2C(OC(C)(C)C)=O)[O:9][C:8](=[O:39])[NH:7]1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[F:43][C:41]1[CH:40]=[C:4]([CH:3]=[C:2]([F:1])[CH:42]=1)[CH2:5][C@H:6]1[C@@H:10]([C@H:11]2[CH2:20][C:19]3[C:14](=[C:15]([O:21][Si:22]([CH:29]([CH3:30])[CH3:31])([CH:23]([CH3:24])[CH3:25])[CH:26]([CH3:27])[CH3:28])[CH:16]=[CH:17][CH:18]=3)[CH2:13][NH:12]2)[O:9][C:8](=[O:39])[NH:7]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67272744HCID 67272744, compound

Product 1

HCID 67271991HCID 67271991, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of (R)-tert-butyl 3-((4S,5S)-4-(3,5-difluorobenzyl)-2-oxooxazolidin-5-yl)-8-(triisopropylsilyloxy)-3,4-dihydroisoquinoline-2(1H)-carboxylate (Step F (11), 470 mg) in CH2Cl2 (20 mL) was treated with TFA (5 mL). This reaction mixture was stirred at rt for 3 h. The mixture was then concentrated in vacuo. Ethyl acetate (10 mL) was added and removed and toluene (10 mL) was added and removed twice to give the title compound: 1H NMR (CDCl3, 500 MHz) δ 1.10 (18H, m), 1.30 (3H, m), 2.61-2.66 (2H, m), 3.08 (1H, dd, J=5, 15 Hz), 3.18 (1H, m), 3.36 (1H, m), 3.79 (1H, d, J=20 Hz), 4.05-4.09 (1H, m), 4.14 (1H, d, J=20 Hz), 4.39 (1H, m), 5.54 (1H, s), 6.64 (1H, d, J=5 Hz), 6.69-6.72 (2H, m), 6.78 (2H, m), 7.01 (1H, m). MS (ESI) (M+H)+ 517.11.

Workup

  1. concentrationThe mixture was then concentrated in vacuo
  2. additionEthyl acetate (10 mL) was added
  3. customremoved
  4. additiontoluene (10 mL) was added
  5. customremoved twice

Sources & evidence

ORD record
ord-7a4ab117dbba48eb92eb4f1ee7431edf
Source dataset
uspto-grants-2011_03
Patent number
US07902218B2

Reaction notes

Loading…