Potassium Hydroxide → HCID 86680737, compound

HRID 1910459Notes

Reaction equation

HRID 1910459 reaction equation
[O:1]=[S:2]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[CH2:6][N:5]([C:13]2[N:18]=[C:17]([NH:19][C@H:20]3[C@H:24]([F:25])[CH2:23][N:22](C(OCC4C=CC=CC=4)=O)[CH2:21]3)[C:16]3[S:36][C:37]([CH3:39])=[CH:38][C:15]=3[N:14]=2)[CH2:4][CH2:3]1.[OH-].[K+]>CO>[F:25][C@@H:24]1[CH2:23][NH:22][CH2:21][C@H:20]1[NH:19][C:17]1[C:16]2[S:36][C:37]([CH3:39])=[CH:38][C:15]=2[N:14]=[C:13]([N:5]2[CH2:6][C:7]3[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=3[S:2](=[O:1])[CH2:3][CH2:4]2)[N:18]=1

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 86680738HCID 86680738, compound

Product 1

HCID 86680737HCID 86680737, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a suspension of benzyl trans-(±)-3-{[2-(1-oxido-2,3-dihydro-1,4-benzothiazepin-4(5H)-yl)-6-methylthienopyrimidin-4-yl]amino}-4-fluoropyrrolidine-1-carboxylate (320 mg, 0.57 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 white solid. MS obsd. (ESI+) [(M+H)+] 432, 1H NMR (400 MHz, METHANOL-d4) δ ppm 7.72 (m, 2H), 7.48 (m, 2H), 6.83 (s, 1H), 5.18-5.38 (m, 1H), 4.66-4.99 (m, 5H), 3.26-3.5 (m, 6H), 2.50 (s, 3H).

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-74a558e0d12e485c89fe04ebc171cfbf
Source dataset
uspto-grants-2013_12
Patent number
US08604019B2

Reaction notes

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