4-Butoxybenzoic acid → HCID 11524913, compound

HRID 1695522Notes

Reaction equation

HRID 1695522 reaction equation
[B-](F)(F)(F)F.CCOC(C(C#N)=NOC(N(C)C)=[N+](C)C)=O.C(N(C(C)C)C(C)C)C.[C@H:32]1([CH2:42][O:43][C:44]2[CH:49]=[CH:48][C:47]([NH2:50])=[CH:46][CH:45]=2)[C@@H:41]2[N:36]([CH2:37][CH2:38][CH2:39][CH2:40]2)[CH2:35][CH2:34][CH2:33]1.[CH2:51]([O:55][C:56]1[CH:64]=[CH:63][C:59]([C:60](O)=[O:61])=[CH:58][CH:57]=1)[CH2:52][CH2:53][CH3:54]>CN(C=O)C.C(=O)(O)[O-].[Na+].C(OCC)(=O)C>[CH2:51]([O:55][C:56]1[CH:57]=[CH:58][C:59]([C:60]([NH:50][C:47]2[CH:48]=[CH:49][C:44]([O:43][CH2:42][C@H:32]3[C@@H:41]4[N:36]([CH2:37][CH2:38][CH2:39][CH2:40]4)[CH2:35][CH2:34][CH2:33]3)=[CH:45][CH:46]=2)=[O:61])=[CH:63][CH:64]=1)[CH2:52][CH2:53][CH3:54]

Participants

8

Reactant 4

HCID 729714-Butoxybenzoic acidHCID 81531DiisopropylethylamineHCID 2733286O-[(Ethoxycarbonyl)cyanomethylenamino]-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 66879100HCID 66879100, compound

Product 1

HCID 11524913HCID 11524913, compound

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolventHCID 516892Sodium BicarbonateSolvent

Procedure

TOTU (78 mg) and ethyldiisopropylamine (31 mg), followed by 4-[(1R,9aR)-1-(octahydroquinolizin-1-yl)methoxy]phenylamine (62 mg), were added to a solution of 4-butoxybenzoic acid (46.4 mg) in DMF (2 ml) at 0° C. After a reaction time of three hours at room temperature, the mixture was diluted with sodium bicarbonate solution and ethyl acetate. After separation of the phases, the aqueous phase was extracted with ethyl acetate, and the combined organic phases were dried over magnesium sulfate and concentrated. The residue was purified by preparative HPLC. The product with the molecular weight of 436.60 (C27H36N2O3); MS (ESI): 437 (M+H+) was obtained in this way.

Workup

  1. customAfter separation of the phases
  2. extractionthe aqueous phase was extracted with ethyl acetate
  3. dry with materialthe combined organic phases were dried over magnesium sulfate
  4. concentrationconcentrated
  5. customThe residue was purified by preparative HPLC
  6. customMS (ESI): 437 (M+H+) was obtained in this way

Sources & evidence

ORD record
ord-fc6fa48afc054918a731041046f8dafe
Source dataset
uspto-grants-2012_04
Patent number
US08163741B2

Reaction notes

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