4-Methylmorpholine → HCID 24945577, compound

HRID 2090819Notes

Reaction equation

HRID 2090819 reaction equation
Cl.O.[NH:3]1[CH2:8][CH2:7][C:6](=[O:9])[CH2:5][CH2:4]1.[CH2:10](N(CC)CC)C.CN1CCOCC1.[CH3:24][O:25][C:26]1[CH:31]=[C:30]([CH3:32])[C:29]([S:33]([N:36]2[CH2:40][CH2:39][CH2:38][CH:37]2[CH2:41][O:42][CH2:43][C:44]([OH:46])=O)(=[O:35])=[O:34])=[C:28]([CH3:47])[CH:27]=1.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1>CN(C)C=O>[CH3:24][O:25][C:26]1[CH:27]=[C:28]([CH3:47])[C:29]([S:33]([N:36]2[CH2:40][CH2:39][CH2:10][CH2:38][CH:37]2[CH2:41][O:42][CH2:43][C:44]([N:3]2[CH2:8][CH2:7][C:6](=[O:9])[CH2:5][CH2:4]2)=[O:46])(=[O:35])=[O:34])=[C:30]([CH3:32])[CH:31]=1

Participants

7

Reactant 5

HCID 79724-MethylmorpholineHCID 8471TriethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 2723901PiperonylamineHCID 597464542-((1-(4-Methoxy-2,6-dimethylphenylsulfonyl)pyrrolidin-2-yl)methoxy)acetic acid

Product 1

HCID 24945577HCID 24945577, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-piperidone monohydrate hydrochloride (260 mg, 2.692 mmol), triethylamine (0.560 ml, 4.038 mmol) and then 4-methylmorpholine (1.62 ml, 14.805 mmol) were added to a solution of 2-((1-(4-methoxy-2,6-dimethylphenylsulfonyl)pyrrolidin-2-yl)methoxy)acetic acid (acid structural unit S27) (1.0 g, 2.692 mmol) in N,N-dimethylformamide (20 ml). Benzotriazol-1-yloxytris(dimethylamino)phosphonium hexafluorophosphate (1.42 g, 3.230 mmol) was then added to the mixture, and stirring was carried out for 3 d at room temperature. The mixture was then concentrated in vacuo, and the residue was taken up in ethyl acetate (30 ml) and saturated sodium hydrogen carbonate solution (20 ml); the aqueous phase was extracted with ethyl acetate (4×10 ml). The combined organic phases were washed with saturated sodium hydrogen carbonate solution (20 ml) and saturated sodium chloride solution (20 ml), dried (MgSO4), and concentrated in vacuo. The crude product was purified by column chromatography (silica gel) using diethyl ether/dichloromethane/ammonia solution (25% aq.) (100:100:2). Yield: 430 mg (35%); MS, m/z 540.3 (MH+)

Workup

  1. concentrationThe mixture was then concentrated in vacuo
  2. extractionthe aqueous phase was extracted with ethyl acetate (4×10 ml)
  3. washThe combined organic phases were washed with saturated sodium hydrogen carbonate solution (20 ml) and saturated sodium chloride solution (20 ml)
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated in vacuo
  6. customThe crude product was purified by column chromatography (silica gel)

Sources & evidence

ORD record
ord-7bc2fdea489a4caa82aea586deb8207e
Source dataset
uspto-grants-2013_05
Patent number
US08435978B2

Reaction notes

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