Trifluoroacetic acid → HCID 67006642, compound

HRID 1047506Notes

Reaction equation

HRID 1047506 reaction equation
FC(F)(F)C(O)=O.C(OC(=O)[NH:14][CH2:15][C:16]([N:18]1[CH:31]2[C:22]([S:34]([C:37]3[CH:42]=[CH:41][C:40]([Cl:43])=[CH:39][CH:38]=3)(=[O:36])=[O:35])([C:23]3[C:28]([O:29][CH2:30]2)=[C:27]([F:32])[CH:26]=[CH:25][C:24]=3[F:33])[CH2:21][CH2:20][CH2:19]1)=[O:17])(C)(C)C>ClCCl>[NH2:14][CH2:15][C:16]([N:18]1[CH:31]2[C:22]([S:34]([C:37]3[CH:38]=[CH:39][C:40]([Cl:43])=[CH:41][CH:42]=3)(=[O:35])=[O:36])([C:23]3[C:28]([O:29][CH2:30]2)=[C:27]([F:32])[CH:26]=[CH:25][C:24]=3[F:33])[CH2:21][CH2:20][CH2:19]1)=[O:17]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67006543HCID 67006543, compound

Product 1

HCID 67006642HCID 67006642, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (2 mL, 27.0 mmol) was dissolved in 16 ml of dichloromethane. The solution was added to {2-[4a-(4-Chloro-benzenesulfonyl)-5,8-difluoro-2,3,4,4a,10,10a-hexahydro-9-oxa-1-aza-phenanthren-1-yl]-2-oxo-ethyl}-carbamic acid tert-butyl ester (260 mg, 0.467 mmol). The solution was stirred at room temperature overnight. The reaction was quenched by washing with Sat. sodium carbonate solution. The organic layer was dried over sodium sulfate and concentrated. Yield: 20.0 mg, 9%. %. 1H NMR (CDCl3 400 MHz) δ 7.62 (d, J=8.1 Hz, 2H), 7.45 (d, J=8.8 Hz, 2H), 7.06 (td, J=8.8, 4.4 Hz, 1H), 6.61-6.52 (m, 1H), 5.41 (bs, 1H), 4.52 (dd, J=11.0, 3.7 Hz, 1H), 4.21 (dd, J=11.7, 5.1 Hz, 1H), 3.53 (bs, 2H), 2.86 (bs, 1H), 2.70-2.61 (m, 1H), 2.55-2.45 (m, 1H), 2.15-2.03 (m, 1H), 1.75-1.44 (m, 4H).

Workup

  1. customThe reaction was quenched
  2. washby washing with Sat. sodium carbonate solution
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-a4a2db4b4a1946c6a924b5088a85ec43
Source dataset
uspto-grants-2013_10
Patent number
US08569521B2

Reaction notes

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