Trifluoroacetic acid → HCID 71255090, compound

HRID 540150Notes

Reaction equation

HRID 540150 reaction equation
[OH:1][CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:36]=[CH:35][C:9]2[CH2:10][N:11]([C:17]3[CH:26]=[C:25]([NH:27]C(=O)OC(C)(C)C)[C:24]4[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=4)[N:18]=3)[CH2:12][CH2:13][S:14](=[O:16])(=[O:15])[C:8]=2[CH:7]=1.FC(F)(F)C(O)=O>ClCCl.O>[NH2:27][C:25]1[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[N:18]=[C:17]([N:11]2[CH2:10][C:9]3[CH:35]=[CH:36][C:6]([O:5][CH2:4][CH2:3][CH2:2][OH:1])=[CH:7][C:8]=3[S:14](=[O:15])(=[O:16])[CH2:13][CH2:12]2)[CH:26]=1

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86691392HCID 86691392, compound

Product 1

HCID 71255090HCID 71255090, compoundYield 4.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture solution of tert-butyl {2-[8-(3-hydroxypropoxy)-1,1-dioxido-2,3-dihydro-1,4-benzothiazepin-4(5H)-yl]quinolin-4-yl}carbamate (359.1 mg, the crude product of the above step) and trifluoroacetic acid (1.0 mL) in dichloromethane (2.0 mL) was stirred at room temperature for 6 hours. The reaction mixture was diluted with water (10 mL) and extracted with ethyl acetate (100 mL). The organic layer was washed with brine (50 mL×2), dried over anhydrous sodium sulfate and concentrated in vacuo. The residue was purified by preparative HPLC to afford 14.2 mg of the desired product as a white solid (yield was 4.9%). MS obsd. (ESI+) [(M+H)+] 414, 1HNMR ((400 MHz, CD3OD) δ ppm 7.82-7.67 (m, 2 H), 7.54-7.48 (m, 2 H), 7.48-7.39 (m, 1 H), 7.19-7.06 (m, 2 H), 6.30 (s, 1 H), 5.04 (s, 2 H), 4.78-4.34 (m, 2 H), 4.11 (t, J=6.32 Hz, 2 H), 3.71 (t, J=6.19 Hz, 2 H), 3.62-3.49 (m, 2 H), 2.11-1.78 (m, 2 H).

Workup

  1. extractionextracted with ethyl acetate (100 mL)
  2. washThe organic layer was washed with brine (50 mL×2)
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-4080195c444f4995880b0710072b3b63
Source dataset
uspto-grants-2014_10
Patent number
US08871756B2

Reaction notes

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