p-Toluenesulfonic acid → HCID 68988102, compound

HRID 69461Notes

Reaction equation

HRID 69461 reaction equation
O1[C:5]2([CH2:9][CH2:8][N:7]([C:10]3[CH:15]=[CH:14][C:13]([N:16]4[CH2:25][CH2:24][C:23]5[C:18](=[CH:19][CH:20]=[C:21]([O:26][CH2:27][C@@H:28]6[CH2:32][CH2:31][CH2:30][O:29]6)[CH:22]=5)[C:17]4=[O:33])=[CH:12][C:11]=3[F:34])[CH2:6]2)[O:4]CC1.C1(C)C=CC(S(O)(=O)=O)=CC=1>CC(C)=O.O>[F:34][C:11]1[CH:12]=[C:13]([N:16]2[CH2:25][CH2:24][C:23]3[C:18](=[CH:19][CH:20]=[C:21]([O:26][CH2:27][C@@H:28]4[CH2:32][CH2:31][CH2:30][O:29]4)[CH:22]=3)[C:17]2=[O:33])[CH:14]=[CH:15][C:10]=1[N:7]1[CH2:8][CH2:9][C:5](=[O:4])[CH2:6]1

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 68992282HCID 68992282, compound

Product 1

HCID 68988102HCID 68988102, compound

Reagents, catalysts & solvents 1

HCID 18366337Propan-2-one--water (1/1)Solvent

Conditions

Temperature
70 °C

Procedure

A mixture of 2-[4-(1,4-dioxa-7-aza-spiro[4.4]non-7-yl)-3-fluorophenyl]-6-[(S)-1-(tetrahydrofuran-2-yl)methoxy]-3,4-dihydro-2H-isoquinolin-1-one (8.4 g) and p-toluenesulfonic acid (3.4 g) in acetone/water (80 mL/40 mL) was heated for 12 h at 70° C. Then the acetone was removed in vacuum and the aqueous phase was neutralized with sodium hydrogencarbonate solution and then extracted several times with ethyl acetate. The organic phases were combined, dried over sodium sulfate and the solvent was removed in vacuum. In this way the product was obtained with molecular weight 424.47 (C24H25FN2O4); MS (ESI): 425 (M+H+).

Workup

  1. customThen the acetone was removed in vacuum
  2. extractionextracted several times with ethyl acetate
  3. dry with materialdried over sodium sulfate
  4. customthe solvent was removed in vacuum
  5. customIn this way the product was obtained with molecular weight 424.47 (C24H25FN2O4)

Sources & evidence

ORD record
ord-ad83ca4a916b450ea9ee7c3e86fcb9db
Source dataset
uspto-grants-2014_09
Patent number
US08822495B2

Reaction notes

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