Potassium Hydroxide → HCID 71255858, compound

HRID 540134Notes

Reaction equation

HRID 540134 reaction equation
[O:1]=[S:2]1(=[O:41])[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[CH2:6][N:5]([C:13]2[CH:22]=[C:21]([NH:23][C@H:24]3[C@H:28]([F:29])[CH2:27][N:26](C(OCC4C=CC=CC=4)=O)[CH2:25]3)[C:20]3[C:15](=[CH:16][CH:17]=[C:18]([CH3:40])[CH:19]=3)[N:14]=2)[CH2:4][CH2:3]1.[OH-].[K+]>CO>[O:41]=[S:2]1(=[O:1])[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[CH2:6][N:5]([C:13]2[CH:22]=[C:21]([NH:23][C@H:24]3[C@H:28]([F:29])[CH2:27][NH:26][CH2:25]3)[C:20]3[C:15](=[CH:16][CH:17]=[C:18]([CH3:40])[CH:19]=3)[N:14]=2)[CH2:4][CH2:3]1

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 86691389HCID 86691389, compound

Product 1

HCID 71255858HCID 71255858, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a suspension of benzyl trans-3-{[2-(1,1-dioxido-2,3-dihydro-1,4-benzothiazepin-4(5H)-yl)-6-methylquinolin-4-yl]amino}-4-fluoropyrrolidine-1-carboxylate (320 mg, 0.557 mmol) in methanol (5 mL) was added an aqueous solution of potassium hydroxide (40%, 5 mL). The suspension was heated under reflux for 30 minutes. The organic solvent was removed by concentration in vacuo. The residue was purified by preparative HPLC to afford the pure product as a solid. MS obsd. (ESI+) [(M+H)+] 441, 1H NMR (400 MHz, CD3OD) δ ppm 8.01 (d, J=6.57 Hz, 1 H), 7.85 (d, J=7.33 Hz, 1 H), 7.67 (s, 1 H), 7.63 (t, J=7.07 Hz, 1 H), 7.53-7.40 (m, 2 H), 7.30 (d, J=8.84 Hz, 1 H), 6.18 (s, 1 H), 5.15 (s, 2 H), 5.10 (brs, 1 H), 4.97 (brs, 1 H), 3.60 (dd, J=12.00, 6.44 Hz, 3 H), 3.28 (brs, 1 H), 3.23 (dd, J=8.84, 5.31 Hz, 1 H), 3.18-3.12 (m, 1 H), 3.04 (dd, J=12.00, 4.67 Hz, 1 H), 2.42 (s, 3 H).

Workup

  1. temperatureThe suspension was heated
  2. temperatureunder reflux for 30 minutes
  3. customThe organic solvent was removed by concentration in vacuo
  4. customThe residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-6747bc0db9ef4e1e98365bcb84944e4b
Source dataset
uspto-grants-2014_10
Patent number
US08871756B2

Reaction notes

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