Trifluoroacetic acid → HCID 178441325, compound

HRID 78550Notes

Reaction equation

HRID 78550 reaction equation
[C:1]([C:5]1[S:9]/[C:8](=[N:10]\[C:11]([C:13]2[CH:31]=[C:30]([C:32]([F:35])([F:34])[F:33])[CH:29]=[CH:28][C:14]=2[O:15][C@@H:16]2[CH2:20][CH2:19][N:18](C(OC(C)(C)C)=O)[CH2:17]2)=[O:12])/[N:7]([CH2:36][C@H:37]2[CH2:41][CH2:40][CH2:39][O:38]2)[CH:6]=1)([CH3:4])([CH3:3])[CH3:2].FC(F)(F)C(O)=O>ClCCl>[C:1]([C:5]1[S:9]/[C:8](=[N:10]\[C:11](=[O:12])[C:13]2[CH:31]=[C:30]([C:32]([F:35])([F:33])[F:34])[CH:29]=[CH:28][C:14]=2[O:15][C@@H:16]2[CH2:20][CH2:19][NH:18][CH2:17]2)/[N:7]([CH2:36][C@H:37]2[CH2:41][CH2:40][CH2:39][O:38]2)[CH:6]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 178452037HCID 178452037, compound

Product 1

HCID 178441325HCID 178441325, compoundYield 90.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of Example 384A (1.223 g, 2.046 mmol) in dichloromethane (5 mL) was added 2,2,2-trifluoroacetic acid (2.333 g, 20.46 mmol). The mixture was stirred at room temperature for 2 hr and then concentrated. The mixture was taken up in dichloromethane and washed with sodium bicarbonate. The organic layers were combined, dried and concentrated to give the title compound (0.92 g, 90%). 1H NMR (300 MHz, CDCl3) δ ppm 1.37 (s, 9H) 1.58-1.72 (m, 1H) 1.79-1.94 (m, 2H) 2.01-2.15 (m, 3H) 2.96-3.06 (m, 2H) 3.23-3.34 (m, 2H) 3.74-3.89 (m, 2H) 4.14-4.21 (m, 1H) 4.24-4.32 (m, 1H) 4.39-4.46 (m, 1H) 4.97-5.03 (m, 1H) 6.88 (s, 1H) 7.05 (d, J=8.73 Hz, 1H) 7.60 (dd, J=8.72, 2.38 Hz, 1H) 8.17 (d, J=2.38 Hz, 1H); MS (DCI/NH3) m/z 498 (M+H)+. Anal. calcd C24H30F3N3O3S.1.2 H2O: C, 55.52; H, 6.29; N, 8.09. Found: C, 55.39; H, 6.63; N, 8.01.

Workup

  1. concentrationconcentrated
  2. washwashed with sodium bicarbonate
  3. customdried
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-16d5799e53ad4b599b603d2243c6e357
Source dataset
uspto-grants-2014_09
Patent number
US08841334B2

Reaction notes

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